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HIGHLAND PARK, IL

What a Bluff

Get your walking shoes and stroll through this forest preserve that runs along the Lake Michigan coastline. You'll walk through deep ravines and 80 foot bluffs looking over the lake.

01 The Bluffs
02 The Ravine
ROGERS PARK

Rogers Park Store Hop

Up in Rogers Park, it’s easy to find things to do. Perhaps not the first place many think to visit on a weekend day off work, Chicago’s northernmost neighborhood has a little bit of everything, from tapas restaurants and trendy coffee shops to lakeside relaxation and charming avenues. Today, we’re going to get a taste of Rogers Park by embarking on an excursion via the Red Line. We’ll stop to pursue antiques, pick out new books and be introduced to witchcraft — all right after fueling up at a cozy, plant-filled cafe.

01 Sol Cafe
02 Lost Eras
03 Lakeside Treasures
04 The Armadillo's Pillow
05 Malliway Bros
NORTH CENTER

A Mighty Rhine Time with Friends

Oktoberfest celebrations come and go, but this guide lets you enjoy German festive cheer all year round. This guide takes you through Chicago's North Side for a German food and beer crawl. You'll throw back beer steins and munch on liver pate, Bavarian steaks, sauerkraut, goulash, and schnitzel. Here are the details.

01 Laschet's Inn
02 Resi's Bierstube
03 Prost!
LINCOLN SQUARE

Ope, It’s Lincoln Square

Stepping into Lincoln Square is like stepping into Chicago’s own fairytale small town. The main strip along Lincoln Avenue has the charm of a European village, with open plazas where locals gather, vintage lampposts casting a warm glow, and storefronts with colorful awnings inviting you in. This guide will lead you through some neighborhood gems, starting with a shop that embodies Chicago’s quirky, no-nonsense pride, stocked with cheeky souvenirs and local art. Next, step back in time at a 19th-century apothecary filled with rare European skincare treasures and a staff that makes every visit feel personal. Finally, end your day with a cone from a plant-based creamery that’s mastered oat-based decadence.

01 Midwest Nice
02 Merz Apothecary
03 Vaca's Creamery
BUCKTOWN

Bucktown Hamburgers & Haunts

A lot of record shops in Chicago are worth visiting, but none are as memorable as the one you’ll be visiting in this guide. It doubles as a “Museum of Curiosities” complete with taxidermy creations, a room on cults and secret societies, and a John Wayne Gacey exhibit (featuring none other than a recreation of his death row prison cell). To continue the theme of lesser known, more eccentric Bucktown gems, you'll dine at a retro pizza joint with a 1980s theme and enjoy a beer at a wonderfully quirky bar and live music venue with a long history in the neighborhood.

01 The StopAlong
02 Graveface
03 Gallery Cabaret
GREEKTOWN

It’s All Greek To Me

Greektown is a unique gem of a neighborhood, rich with Greek food and community. Located just west of downtown, it’s a place where Old World traditions mix with modern-day culture. To get to know the area, you’ll fuel up with coffee, take a stroll in a park and end with a traditional Greek dinner.

01 Ground Up Coffee
02 Mary Bartelme Park
03 Athena Greek Restaurant
LOGAN SQUARE

Dinner With a Side of Improv

For less than the price of a cup of coffee, you can go see one of the best improv shows that Chicago has to offer. This evening, you’ll sandwich that show between some delicious craft cocktails at a neighborhood watering hole and dinner at a quaint bistro with a Michelin nod, all within a four-block stretch on West Diversey Avenue.

01 Quality Time
02 Logan Square Improv
03 Cellar Door Provisions
THE LOOP

On The (Maggie) Daley (Park)

Amid the frenzy of the city, downtown Chicago offers prominent green spaces for visitors and locals alike to enjoy. It's like you're getting out of the city, while in reality, you're going deeper into it. With today's guide, you'll get an opportunity to see the city in a new way — quite literally. You’ll get out to one of the Loop's most unique parks to traverse a wall overlooking the concrete jungle that is Chicago, followed by a nearby picnic and a few touristy delights.

01 Maggie Daley Park
02 Hot Woks Cool Sushi
ANDERSONVILLE

Andersonville or Booksville?

Andersonville is a literary hub, where bibliophiles and casual book browsers alike will delight in a variety of distinct bookstores. This exploration brings you to three unique shops, just half a mile away from each other. You’ll grab coffee at a theater-focused cafe, wander a few blocks to a feminist bookstore and end at an oasis for used and rare books.

01 The Understudy
02 Women & Children First
03 Uncharted Books
BRONZEVILLE

Intellect And Wine

To follow this guide, you’re heading south to the historic and beautiful Bronzeville neighborhood. Combining books, music and history, you’ll expand your mind and latch onto some shining nuggets of Chicago history. What could be better? Oh, and then you’ll follow it up with a glass (or bottle) of wine and a lovely meal at one of the neighborhood’s premiere eateries.

01 Da Book Joint
02 Chicago Hip Hop Heritage Museum
03 Bronzeville Winery
LAKEVIEW

Celluloid And Sandwiches

There’s nothing quite as satisfying as watching an outdoor movie accompanied by a cool, summer breeze at the tail end of a scorching Chicago summer day. Pair that with an upscale diner meal and a round of drinks inside a lounge dedicated to movie lovers and you have a recipe for a perfect summer evening.

01 Little Goat Diner
02 Music Box Lounge
03 Music Box Garden
THE LOOP

How To Become An Expert About Chicago

Chicago’s Riverwalk is a labyrinth of life in the heart of downtown. The 1.25-mile-long path, which was expanded in 2016, offers unique city views and plenty of activities for all ages. It’s perhaps best enjoyed on the river itself, which is where today’s guide sets off. You’ll start with a scenic and educational boat tour, then cool off with homemade gelato.

01 Wendella Tours & Cruises
02 Sweet Home Gelato
LINCOLN PARK

A $10 Day In Lincoln Park

Remaining frugal in a city like Chicago can be a tough task, but it’s not impossible. To prove it’s doable, we ventured to Lincoln Park, a notably expensive Chicago neighborhood, to craft a memorable outing on a $10 budget. You’ll start by grabbing a coffee drink in a small coffee shop, followed by a trip to a classic Chicago-style establishment for a bite to eat. You’ll then head to a French-inspired dessert shop before ending the day with a tour of a historic Chicago architectural monument. Plus, all are within walkable distances from one another. You won’t have to break the bank to enjoy a day in the city.

01 Ludlow Charlingtons Coffee Shop
02 Angry Octopus
03 Vanille Patisserie
04 Charnley-Persky House Museum
WICKER PARK

Handmade On Division

This lineup is for those in serious need of a dopamine hit. The night takes you along Division Street, where you’ll be surrounded by twinkly lights and al fresco dining. From glittery gemstones to a decadent handmade pasta dish and live music, this guide lays out an evening of mood-boosters. Pop into these three establishments for a night on the town that you probably need.

01 Beadniks
02 Tortello
03 Phyllis' Musical Inn
SAUGATUCK, MICHIGAN

Saugatuck Day Two

Day one of your Saugatuck trip focused on enjoying locally farmed cider and exploring the bustling town by water. On day two, you’ll explore by sand and indulge in some culinary delights by local chefs and distillers.

01 Saugatuck Dune Rides
02 The Southerner
03 Coppercraft Distillery Tasting Room
SAUGATUCK, MICHIGAN

Saugatuck Day One

Drive south along Lake Michigan and you’re sure to pass through dozens of cute beach towns. But about 145 miles around the lake from Chicago, you’ll find one of the most charming and unique coastal towns in Michigan called Saugatuck. Known as a haven for artists and the LGBTQ+ community, you will spend two days exploring the impressive arts and culinary scenes as well as the natural treasures of Saugatuck, learning why thousands of vacationers flock to the area each year.

01 Virtue Cider
02 The Butler
03 The Star of Saugatuck
NORTH CENTER

Up A Lazy River

Few things symbolize summer like ice cream and boating, and Chicago offers myriad options to embrace them both. The Chicago River cuts through the city’s urban sprawl with 156 miles of water, and today you'll get busy exploring it. You’ll start the afternoon in nature at a North Center boathouse and end by treating yourself to sweets at one of Chicago’s oldest and most iconic ice cream parlors.

01 Chicago River Canoe & Kayak
02 Margie's Candies
PILSEN

Pilsen’s Bread (Tacos) And Butter (Beer)

Some of the best meals in Chicago can be found in nondescript, no-frills establishments, it turns out. This itinerary will guide you through exploring one of the city’s most vibrant neighborhoods with deep cultural roots by starting with street tacos at a market and wrapping up the day enjoying one of the city’s newest breweries, all within Pilsen.

01 Carniceria Maribel
02 Monochrome Brewing
LITTLE INDIA

Down The Block But Across The Pacific

As one of Chicago’s most ethnically mixed neighborhoods, West Ridge is a melting pot of cultures and flavors. This diversity is perhaps most prevalent on Devon Avenue, where global cuisines blend seamlessly with a strong community feel. Tonight’s escapade gives you a sampling of the area’s eats and treats along a stretch known as Little India. You’ll feast on vegetarian food, indulge in dessert and take in some live music at a neighborhood bar.

01 Uru-Swati
02 Sukhadia’s Sweets and Snacks
03 Cary’s Lounge
AVONDALE

Row, Row, Row Your Boat Up The Chicago River

Lake Michigan and the downtown parts of the Chicago River may get all the glory, but the northern branch of the river is a stone you shouldn’t leave unturned. From a boat ride to some whiskey tasting and a delicious Indian dinner, this guide will bring you through some of the river’s lesser-known, but just as noteworthy, spots.

01 Chicago Electric Boat Company Rental
02 Judson and Moore Distillery
03 Thattu
IRVING PARK

Dog Days of Summer

Everyone knows humans don’t deserve dogs. But you can show some appreciation to your four-legged friend by bringing them with you on this dog-friendly bar crawl in Irving Park. You’ll hit a Chicago sports bar with an affinity for dogs, a cider house with a sprawling patio for some bites, and finally a quintessential dive bar with a cabin-like interior, all while tasting beers and collecting dog pets along the way.

01 The Booze Hound
02 Eris Brewery and Cider House
03 The Cabin at Old Irving
SOUTH LOOP

Walk Back In Time For A Root Beer And Reuben

Did you know that just half a mile away from the bustling Magnificent Mile you can step back in time to an age of double-decker, decadent diners? That's where you'll spend a pleasurable afternoon. But before you do, you'll begin your outing with top-notch coffee and walk through a serene European-feeling garden.

01 Necessary & Sufficient Coffee
02 Logan Garden
03 Eleven City Diner
HUMBOLDT PARK

Will Paddle For Cake

As the summer heat hits Chicago, you’ll naturally be jonesing for two things: a sweet treat and time in the hot, outdoor air. In this guide, you’ll get both. Start the day at one of the oldest (and cutest) bakeries in Chicago before making your way across the street to catch some rays and hop on a pedal boat at one of the city’s most iconic parks.

01 Roeser's Bakery
02 Humboldt Park Lagoon
NEAR NORTH SIDE

Work From Coffee Shops

Remote work has its perks, and today, you're going to make the most of them. Pack your laptop, headphones and notebooks and head to the Near North Side, where you'll split your day between two cafes, one specializing in Croatian eats and the other a "sanctuary for the wandering soul." You'll take your last meeting at the final destination: a modern outpost serving cocktails overlooking the Chicago River.

01 Doma Cafe
02 Nomad Chicago
03 Marshall's Landing
LOGAN SQUARE

Southwest Eats and Basement Drinks

Tonight, you're going to head into Logan Square for dinner at one of the neighborhood's only rooftop patios and drinks at some "if you know, you know" bars. You'll start off the outing with Mexican food and a cocktail in a setting that’ll leave you booking a flight to Cabo. Not only that, but what looks like a normal restaurant from the outside is also home to a speakeasy open only on the weekends. The night will continue with another tucked-away bar where you'll enter a nondescript door lit by a sign with a small bird and question why you ever went to traditional, visible bars in the first place.

01 Lonesome Rose
02 Golden Teardrops
03 Meadowlark
BUCKTOWN

No Wine Left Behind

The weather warms up, so Chicagoans flock to the elevated 606 trail to get steps in and marvel at how lush the city has become. Today, you'll take in the nature by walking two-thirds of the beloved trail and fueling up on natural wine at two charming wine bars along the way. The bars are just two of numerous businesses that are dotted along The 606 trail, which serves four neighborhoods and thousands of locals and visitors each day.

01 Red & White Wines
02 The 606
03 Outside Voices
LAKEVIEW

A Timeless Lakeview Time

Lakeview is an easy draw. Its proximity to the great Lake Michigan, seemingly endless options for food and drinks, and lively music scene make it an ideal place to spend a night out. Tonight’s classic Lakeview evening will bring you down the Southport Corridor where you’ll start with a drink at Corridor Brewery and Provisions before dinner and a show at Coda di Volpe and Schubas Tavern, respectively.

01 Corridor Brewery & Provisions
02 Coda di Volpe
03 Schubas Tavern
THE LOOP

France In Chicago

You daydream of a far-flung vacation — perhaps to France's lavender fields or a romp through Parisian alleys. But flights are steep, and work keeps you at home. No worries. Chicago offers a cultural escape. Today, you’ll take a trip downtown and to its surrounding neighborhoods to enjoy a bit of French culture through breakfast, a pastry run and a treasure hunt.

01 Venteux Brasserie, Cafe & Oyster Bar
02 La Fournette
03 P.O.S.H.
NOBLE SQUARE

Life’s A Picnic

It’s springtime in Chicago, and that means the city is collectively regaining its will to live. To maximize your time in the sun and enjoy the city on a casual afternoon, start at a delicatessen for a gourmet sandwich, charcuterie, snacks, and a bottle of wine. Bring your picnic provisions a short walk away and lay out on a big lawn with the skyline as your backdrop.

01 Tempesta Market
02 Eckhart Park
BUCKTOWN

House (Decor) Hunting

There's nothing quite like the decorating high, as interior designers like to say, you get when hunting for and securing vintage homeware. The hunt is the main part of the thrill, so today you'll head to three female-owned stores across Humboldt Park, Bucktown and Logan Square to chase that feeling and acquire new treasures for the home.

01 Humboldt House
02 Eskell
03 Logan Mercantile
LINCOLN PARK

Well Fed and Well Read in Lincoln Park

After a long week, or to start off a new week on a relaxed note, whichever way you look at it, a peaceful Sunday morning is just what the doctor ordered. To achieve that, you’ll spend your morning in Lincoln Park where you’ll kick off the day with comfort food at Batter & Berries before recharging with some caffeine at Coffee Lab & Roasters. Finally, you’ll escape to another world at Three Avenues Bookshop.

01 Batter & Berries
02 Coffee Lab & Roasters
03 Three Avenues Bookshop
HYDE PARK

Evening Stroll Through Hyde Park

Home to the University of Chicago, Hyde Park is undoubtedly the city’s ideal hub for intellectuals. To tap into your inner highbrow academic, take a trip through the neighborhood for a bookish day filled with daydreaming and fantasies about your other life as a poet or professor. Start at 57th Street Books, then take an obligatory walk around the gothic campus and finish the night with delicious Italian food at Ascione Bistro.

01 57th Street Books
02 University of Chicago
03 Ascione Bistro
ANDERSONVILLE

Andersonville Afternoon

It’s not hard to love Andersonville. It’s a charming North Side pocket of eclecticness and eccentricity just waiting to be tapped. This neighborhood is worth a meandering walk down Clark Street punctuated with sweet treats, quirky thrift finds and a delicious cocktail. In this guide, find a serendipitous balance of all three at a gluten-free bakery, a locally beloved thrift store and an inviting cocktail bar.

01 Defloured
02 Brown Elephant
03 Nobody's Darling
THE LOOP

A Good End to a Rough Week

Work sucks. Alright, maybe not always, but you know what we mean. So, after one of those weeks, it’s only fitting to indulge a bit. After you’ve put your time in for the day and successfully launched your laptop into Lake Michigan, it’s time to treat yourself to a few spots just a hop, skip, and jump from your office amid the bustling rush hours of the Loop. Once you’re clocked out of meetings that probably should’ve been emails, we’ll take a quick stroll out of the office for aptly priced drinks, greasy Chicago delicacies and historic storefronts all within a few blocks of each other.

01 Ceres Cafe
02 Luke's Italian Beef
03 Sky Ride Tap
WEST TOWN

Let’s Go All Together Now

Everyone knows Chicago is one of the best cities for food, comedy and drinks. Tonight, you’ll combine all three for a lively night in the West Town and Wicker Park neighborhoods. You'll start with dinner at a natural wine shop and restaurant for a meal that's described as a fancy picnic. You'll then take in a comedy show at a theater reminiscent of the 1920s Golden Age, featuring ornate Art Deco details, plush velvet seats, and gilded accents. Finish off the night with a drink and a game of pool down the street

01 All Together Now
02 Comedy @ The Den Theatre
03 Drinks @ Little Victories
LINCOLN PARK

Evening Escapades Down Halstead

It’s not uncommon to be overwhelmed by contemporary nightlife spots, so we're going to infuse the night with some rich, old-school history and rhythm right in the heart of Lincoln Park. It starts with dinner at an authentic Sichuan restaurant. After, you’ll find yourself at an iconic Chicago blues bar that’s been around since 1968. Finally, the night caps off with a drink and some dancing at a neighborhood watering hole.

01 Chengdu Impression
02 Kingston Mines
03 aliveOne
RAVENSWOOD

A Few Hops Around Malt Row

Ravenswood, Wrigleyville’s cozy sibling to the north, is home to Chicago’s Malt Row. With Ravenswood Avenue hosting more than 10 craft breweries and distilleries, hitting them all in one go could be quite the doozy. Instead, this guide focuses on two spots for a chill evening of snacks, digestifs and, beer.

01 Dovetail Brewery
02 2. Cultivate
LOGAN SQUARE

Dive Into Logan Square

Life is a constant series of go-go-go, so tonight, you’re in for some lounging in Logan Square.  It starts with a combo vintage store and bar and then a late-night hot dog stand before ending the outing at a longtime community watering hole tended to by the bar's beloved matriarch.

01 Consignment Lounge
02 Mr. E's Late Nite
03 Whirlaway Lounge
LINCOLN PARK

Never-Ending Night

After a week of being responsible and sticking to healthy eating, it's time to indulge a little. This guide kicks off at a fusion Chinese-Korean BBQ spot, followed by a visit to a craft brewery known for its unique selection of beers. The night continues until the early parts of the morning at a nightclub with a history of hosting renowned DJs over the past decade. Surprisingly, all these hot spots are just a brief, 10-minute walk from the Red Line and within a two-minute stroll of each other.

01 Jiang Niu
02 Off Color Brewing
03 PRYSM
MILWAUKEE, WI

Milwaukee Weekend Getaway

It’s time for a change of scenery, so for two days this weekend, we’re heading north to Milwaukee — a mini Chicago, as some refer to it. The vibrant Wisconsin city on the west coast of Lake Michigan is a quick 1.5-hour drive from Chicago. You’ll know you’ve arrived when you’re in view of dozens of steeples scattered about and expressway ramps crisscrossing everywhere you look. The backbone of this excursion is an art museum with otherworldly architecture, a garden conservatory in futuristic domes, a bar in the back of a TV repair shop, and even more good food and drink interspersed throughout.

01 Interval
02 Milwaukee Art Museum
03 Mitchell Park Horticultural Conservatory
04 Don's TV & Repair
05 Likewise
06 Allie Boy's
07 Fischberger's Variety
08 Nonfiction Natural Wines
ROSCOE VILLAGE

Knock Knock..Who’s There?

We’re going on a night time adventure in Roscoe Village for burgers, cocktails, live jazz, and a comedy show in the back of a bar. This isn’t any comedy show. The performers here are the type where 1 or 2 years down the road you’ll be seeing them on a Netflix comedy special and you can brag to all your friends that you discovered them well before they got big. So kudos to your future self for being able to do that.

01 The Region
02 Hungry Brain
03 Beat Kitchen
WEST TOWN

A Cure For the Chicago Winter Blues

As winter firmly grips Chicago in its grasp, we've got a guide to fight back the only way we know how -- day drinking and binge eating. Our guide takes us to one of the city's designated industrial corridors in West Town. It covers over 1,000 acres, mainly filled with warehouses and light manufacturing facilities. But it's also home to a growing and packed beer scene with five breweries and a distillery, all clustered within a mile of each other. You'll visit two breweries, each with a different vibe. Between visits, you'll grab some artisan donuts from a pair of bakers who've set up a space in a coffee roasting facility nearby.

01 Midwest Coast Brewing
02 Brite / Metric Coffee
03 District Brew Yards
PILSEN

Vintage, Vintage, Vintage

Pilsen is a mecca for vintage shoppers and the plan for this guide is to bounce around to four different shops, each with a different era of fashion and merchandise in mind. But before the shopping spree begins, you'll start the day with chilaquiles and coffee at small countertop diner that's been run by a mother and son team for over 30 years.

01 Parkview Restaurant
02 Pilsen Vintage
03 Very Best Vintage
04 Shady Rest Vintage & Vinyl
05 Knee Deep Vintage
EDGEWATER

Edgewater, I’ve Got My Pie on You

This guide takes us to Edgewater for a quick afternoon trip. It starts at a place that's one part pie shop, one part bar, and one part elevated tavern food. Afterward, head across the street to Chicago's oldest antique store. Here are the details.

01 Beard and Belly
02 Broadway Antique Market
NILES, IL

Winter is Coming

For a lot of Chicagoans, it's not about getting used to the cold-weather season but finding ways to cope with it until summer rolls around. This guide is one of those coping mechanisms. You'll spend the day jumping between pools, saunas, and heated relaxation rooms. In between, you'll stay warm with a sizzling bowl of kimchi soup and other Korean eats. 

01 Wet Spa
02 Lounge
03 Food Court
04 Resting Area
LOGAN SQUARE

Need a Date Idea? Yes, And…

Chicago's improv and comedy scene is unrivaled. You can find a show nearly every night of the week, but more often than not, that means hanging out somewhere in Lakeview, Lincoln Park, or thereabouts. For this guide, you'll catch a show on the other side of the Kennedy Expressway. You'll start a small theater in Logan Square making its own name on the Chicago comedy circuit. Afterwards, head up the street for late night patio drinks.

01 Logan Square Improv
02 Ludlow Liquors
KEWASKUM, WI

Pedal to the Kettle

About 18,000 years ago, Illinois and Wisconsin were covered under a big sheet of glacial ice.  Eventually, these massive glaciers began to retreat, but not before leaving behind fields of rock and debris, otherwise known as moraines.  For this guide, you'll take a road trip to see this geological formation, which extends over 120 miles across Wisconsin. You'll make a 2.5-hour drive into Kettle Moraine State Forest, where you'll camp, hike tall ridges, and fish out on the water.

01 Wind Point Light House
02 Kettle Moraine Scenic Drive
03 Long Lake
04 Mount Dundee
05 Parnell Tower
WEST LOOP

Coquette and Catacombs

Sometimes, planning date night is as easy as dinner and a show. The city is chock-full of establishments that would pair perfectly in this category, but tonight, we’re headed to the West Loop for a fancy dinner in a 70s-inspired French eatery followed by a show in a former church brimming with history with a bar in their "catacombs."

01 Coquette
02 Epiphany Center for the Arts
RINGWOOD, IL

Hike Ancient Glacial Formations

Imagine Chicago with mountains in the distance. Nobody would ever leave. While we don't have mountains, there are still places to hike to get some elevation. For this guide, you'll head about 1.5 hours outside the city where you'll hike through 3,400 acres of bogs, wetlands, and up large, ancient land formations called kames.

01 Trail Head
02 Camelback Kame
03 Keystone Road Landing
AVONDALE

Not Just a Coffee Date

Centered around one corner in Avondale, this guide takes your traditional coffee date and mixes it up with an after-hours comedy show followed by beer, board games and a variant of the Italian beef next door.

01 Avondale Coffee Club
02 Beer Temple
GALENA, IL

Galena, IL

This guide has you hitting the road for a weekend trip out of the city. You'll visit Galena, IL, about a three-hour drive from Chicago and on the border between Illinois and Iowa. This is the opposite of the hustle and bustle of Chicago — it’s a small town situated amongst rolling hills, and its big draw is a picturesque main street full of small boutiques and restaurants.

01 Desoto House Hotel
02 Dowling House
03 Durty Gurt's
04 Great American Popcorn Co.
05 Ulysses S. Grant's Home
06 Root Beer Revelry
LEMONT, IL

Morning Hike and Lunch Beneath a Temple

We're taking a short trip outside the city to hike through a 2,500 acre forest preserve. We start by grabbing coffee at a quirky and retro coffee house, then we head to the trail head where we'll hike through rolling hills, waterfalls, and overlooks. We'll then take a detour off the trail to have lunch beneath a Hindu temple. Here are the details.

01 Ashbary Coffee House
02 Waterfall Glen Forest Preserve
03 The Hindu Temple of Greater Chicago
LAKE FOREST, IL

On the Train to Nature

Access to nature can sometimes feel inaccessible if you don't have a car. But for this guide, the Metra is all you need. You'll take the UP-N line to the North Shore where you'll walk through a field of wild flowers on a former military base turned nature preserve. The hike ends on a bluff overlooking Lake Michigan. After, you'll hop back on the Metra and take it one stop where you'll explore a charming downtown and grab a quick bite at a hot dog and sandwich shop. It ends at an old-school ice cream and candy shop for desert.

01 Fort Sheridan Nature Preserve
02 Left Bank
03 Sweets
WICKER PARK

Plant Shop, Plant Food, Plant Gift Shop

If you haven't guessed by the title, this guide is all about plants. It starts at a plant shop in Wicker Park, where you'll not just buy a plant but learn how to keep it alive. You'll then stop for made-from-scratch vegan and vegetarian comfort food next door. Finally, it ends at a moody floral and gift shop where you'll find things you didn't know you needed.

01 Chicago Plants
02 2. Handlebar
03 Asrai Garden
LAKEVIEW

A Purr-ty Fun Date

There's a misconception out there that you're either a dog person or a cat person, and you've got to date someone with a matching preference. For this date idea, however, we'll prove that everyone can be a cat person. We start things off with coffee at a place that looks more like a dive bar than a coffee shop. Afterwards, we head down the street to play video games in a room full of cats. Here are the details.

01 Osmium Coffee
02 The Catcade
WEST TOWN

West Town Walkabout

This is a classic neighborhood walkabout in West Town. It starts with coffee and shopping at a pandemic-inspired retail/coffee shop. You'll then grab a Filipino breakfast at at a place that's going on 30 years in the neighborhood. After, you'll visit a small art gallery focused on contemporary African and African diaspora art. Finally, it all ends with a few beers at a massive brewery nearby.

01 The Center of Order and Experimentation
02 Uncle Mike's Place
03 Marianne Ibrahim Gallery
04 On Tour Brewing
THE LOOP

Picasso and Photos

In a new addition to our “Known/Unknown” series, we’re heading to Michigan Avenue to pair a Chicago landmark with an overlooked place nearby. The first stop is to a grand art institution flanked by iconic bronze lions. Here, masterpieces await. But the exploration doesn't end there. After, you'll walk down the street and visit another 3-story museum delving into the world of contemporary photography and examine a diverse collection of thousands of works from artists around the globe.

01 Art Institute of Chicago
02 Museum of Contemporary Photography
PRINTER'S ROW

Wine Down in Printer’s Row

Wine and book lovers, especially fans of the two combined, this one's for you. You'll venture to Printer’s Row, a neighborhood near the South Loop that makes walking through its charming tree-lined streets akin to a voyage back in time. As its name indicates, Printer’s Row boasts a history intertwined with literature. With old-world energy and activities to match, this guide includes quintessential stops at a pharmacy-turned-wine-bar, a mom-and-pop-owned bookstore and a jazz club that describes itself as being the place “where jazz lives in Chicago.”

01 Sandmeyer's Bookstore
02 Printer's Row Wine Shop
03 Jazz Showcase
LAKE FOREST, IL

A Farm and Savanna on the North Shore

Start your day at a sustainable farm, picking up fresh produce and sipping local coffee. Then, step into a neighboring nature preserve for an easy stroll or a longer hike through a tall grass savanna. End the day at a family-owned brewery, with craft beer paired with a delicious brisket sandwich.

01 Elawa Farm and Market
02 Middlefork Savanna Forest Preserve
03 Overlook
04 Lake Bluff Brewing Co.
WEST RIDGE

Balkan Eats and a Hiking Retreat in West Ridge

This guide has you visiting West Ridge, a quiet residential North Side neighborhood that's home to a vibrant South Asian, Jewish, and Eastern European community. You'll start with a hike on a 20-acre nature preserve, build a wooden fort, and end with Balkan street food.

01 West Ridge Nature Park
02 Toscano
EDGEWATER

Historic Homes & Coffee For Artists In Edgewater

In this guide, you’ll be taking in the history of Edgewater which encompasses several smaller neighborhoods like Edgewater Beach, Edgewater Glen, Magnolia Glen, and Andersonville. You'll take this in both through a museum visit and boots-on-the-ground fieldwork. All good walks should come with rewards, though, and don’t worry: high-quality coffee awaits at the end of this excursion.

01 Edgewater Historical Society
02 The Historic Lakewood-Balmoral District
03 Understudy Coffee and Books
NEW BUFFALO, MICHIGAN

Weekend in New Buffalo

We've got a short trip planned to Southwest Michigan for a quick weekend getaway. You'll layout on dunes along Lake Michigan's coast, drink whiskey while putting on a 30,000-square-foot putting green, get some hiking in, and explore shops along a country highway.

01 The Neighborhood Hotel (Grand Beach)
02 New Buffalo Beach
03 Journeyman Distillery
04 Alapash Mercantile
05 Warren Dunes State Park
06 Whistle Stop Grocery
LOGAN SQUARE

It’s BLT Season

This guide is part of our Good Bites series, and we're venturing out to pick up fresh ingredients to make a classic BLT -- our summer sandwich of choice. While you can head to Mariano's to get ingredients for a decent BLT, we're looking for greatness, and greatness starts with a quality tomato and fresh bread. We're headed to Logan Square on our quest for these items. We begin with a trip to a French cafe to grab bread and to have a morning coffee on the cafe's tree-shaded, side yard patio. Afterwards, we make our way down the block to a Sunday farmers market to get the rest of our BLT provisions.  Here are the details.

01 La Boulangerie
02 Logan Square Farmers Market
HUMBOLDT PARK

Welcome to the Jungle

We've got a house party teed up in Humboldt Park. You're going to catch live music and comedy acts in the basement of a Humboldt Park home. Afterward, you're capping off the night at a local dive bar for a taste of the city's best sandwiches and experience that will leave you wanting more.

01 1. Humboldt Jungle
02 Humboldt Haus
AVONDALE

Giant Dumplings and a Giant Wall of Beer

For this guide you'll be grubbing at the back of a Korean grocery store, and afterwards, you'll take some to-go dumplings and head down the street to one of the largest breweries in Illinois

01 Joong Boo
02 Revolution Brewery
LINCOLN PARK

A One-Mile Food and Art Walk in Lincoln Park

Get your walking shoes ready, because we're going on an old fashioned neighborhood walkabout. The plan for the day is a one mile jaunt through Lincoln Park that's got a bit of an international flare. It starts with Taiwanese bubble tea, then olive oil and lemon drenched Greek chicken and fries, and we end the day at a Chicago apartment building from 1920's that's been converted into an art gallery and cultural center. 

01 Hello Jasmine
02 Oz Park
03 Athenian Room
04 Wrightwood 659
WEST LOOP

From Warehouse to Basement 🔊

The night starts on an empty street surrounded by warehouses where you'll have cocktails inside a bustling taproom while a forklift might be operating in the background. Later into the night, venture to a basement wine bar and restaurant, where the mood is contemporary gothic and the chefs in the small kitchen whip up modern American cuisine, blending an eclectic mix of Caribbean, Asian, and European plates.

01 Wolfpoint Distilling
02 Press Room
LOGAN SQUARE

No Time to Spare, Visit Logan Square

We’re traveling to Fullerton Avenue in Chicago’s Logan Square neighborhood to visit a bowling alley with a rich history as the center of Chicago's punk rock scene in the 90s. Afterward, you'll head to a cheekily named 1920s-style tavern to end the night with well-made cocktails paired with tamales and pizza on the side.

01 Fireside Bowl
02 Spilt Milk
ANDERSONVILLE

Vinyl, Books, and Comics

We’re going music and book shopping in Andersonville today. The great thing about record stores and bookstores is that you don’t have to buy anything to enjoy yourself—browsing covers and reading back summaries, mind racing with anticipation of what’s contained—that’s its own fun. The difficult thing about records and books is you usually want to buy more than your wallet allows. Today, we’re looking at three different shops in Andersonville’s famed commercial district on Clark Street.

01 Rattleback Records
02 Women & Children First
03 Graham Cracker Comics
WICKER PARK

East Coast Pizza, Karaoke, and Giant Cocktails

We've planned a whole night, all within a one-block radius right off the Damen Blue Line Station. It starts with New Haven-style pizza at a brewery with a 20-year history in Wicker Park. You'll then head around the corner, where if you can time it right, you'll have drinks and maybe a bit of karaoke at this bar with an early 20th-century vintage style. The last stop is a speakeasy behind a record store where you'll end the night with a giant cocktail served in a gauntlet.

01 Piece Brewery and Pizzeria
02 Revel Room
03 Dorian's
LINCOLN PARK

A Night Full of Taco Energy 🔊

Ask any group of Chicagoans about their favorite taqueria and you'll get different answer from each. For this guide, you're going to eat at a place that just might make the cut on your list of favorites. You'll then walk a few blocks to a laid-back brewery along the Chicago river with a history of experimental beers. The night ends across the street where the next generation of funny people are hanging out and performing improv.

01 El Tragon
02 Off Color Brewing
03 iO Theater
LAKEVIEW

It’s Showtime in Southport

No matter the weather, it's worth venturing Chicago's Lakeview neighborhood and making several stops on Southport Avenue, a thoroughfare bustling with hip restaurants, popular stores, and theaters. This guide starts with an Argentinean tapas restaurant featuring a wall of wine. You'll then make your way to a theater made for cinephiles looking to partake in the latest film festival, or a century-old live performance venue just a few doors down.

01 Bodega Sur
02 Music Box Theater
WICKER PARK

Winter Retreat in the Heat

No matter how long you've lived in Chicago, there will always be those frigid winter days where you just can't shake the cold. I'm talking about the type of cold that not only has you numb all over but mentally drained too. This guide is going to help you recharge. You'll hang out at a traditional bathhouse to soak in super-heated pools, lounge in oven-scorching banyas, and warm up with a bowl of borscht. Here are the details.

01 Chicago Bath House
02 Dining Room
BUCKTOWN

Work From Bar

If you're part of the work-from-home crowd, I'm guessing that at some point, you may have gone days without stepping foot outside. It's a disconcerting feeling when you realize three days have passed, and you just went through a self-imposed quarantine. To help break up the week and get you out of your work-from-home pajamas, this guide has you spending a work day at a long-time neighborhood bar and coffee shop. You'll then grab lunch at a pizza shop with a history dating back a half-century.

01 Map Room
02 My Pi Pizza
ANDERSONVILLE

Andersonville After Dark

10 pieces of Korean chicken, 30 plays, and 68 draft lines. That's the setup for this evening excursion in Andersonville. It starts with a late dinner featuring bubble tea and double-fried Korean chicken. You'll then go around the corner to watch not one, not two, but 30 different shorts plays crammed into one hour. Finally, you'll catch a night cap at a Belgian-inspired pub known for its 68 draft lines.

01 Cuckoo
02 The Neo-Futurists
03 Hopleaf
PILSEN

Cold Outside, but Hot Pot in Here

When the cold weather strikes, this guide has you cooking up some eats to keep warm -- or should I say hot -- hot pot that is. To get started, you'll head to a mega-sized Chinese grocer in Pilsen to pick up essential hot pot ingredients like fish tofu, lobster balls, udon noodles, sesame paste, and fried chili oil. We've included step-by-step instructions for a successful hot pot party. While there, you'll check out some of the other developments going on inside.

01 88 Marketplace
02 Bao Bae Bakery
03 Meat and Hot Pot Ingredient Section
04 Food Court
THE LOOP

Cheezborgers You Can Write Home About

This itinerary is part of our "Known/Unknown" series, where we pair a Chicago landmark with overlooked places nearby. For fans of literature and architecture, you'll visit two smaller museums near the loop that operate in the shadow of the mega-institutions nearby. Between those stops, you'll spend time underneath Michigan Avenue for "cheeps" and "cheezborgers" at a longstanding tavern wrapped in Chicago nostalgia. This is especially great when you have a random free day to explore spots you've always meant to visit, or if you have family or friends who've done all the main touristy stuff and are coming back on a second or third visit.

01 American Writers Museum
02 Billy Goat Tavern
03 Richard Driehaus Museum
WICKER PARK

Shuffle Your Way Down Wicker Park

This guide has all the necessary ingredients for a terrific Sunday Funday outing. It starts in Wicker Park at a comic-book themed burger joint that pays homage to the "In-N-Out" burger. We then walk down the street to a massive warehouse of over-sized games, shuffleboard courts, and cocktails. The last stop takes you up 13 floors to give you absolutely stunning views of Chicago. Here are the details.

01 The Stop Along
02 Royal Palms Shuffleboard Club
03 3. Up Room (Inside The Robey Hotel)
LOGAN SQUARE

Late-Night Comedy and Cocktails

While the rest of the city sleeps, this guide has you going on a midnight escapade through Logan Square and Bucktown. You'll start at a late-night comedy club and then head down the street for post-show drinks at a chill neighborhood craft cocktail bar. After a long night of laughs and booze, you'll end with deliciously greasy burgers and hot dogs at a corner grill shack open until 3 am on the weekends. Here are the details.

01 Lincoln Lodge
02 Remedy
03 Jr's Redhots
UPTOWN

Gone Fishing

We're taking advantage of living next to a giant freshwater lake and have you going on a fishing 101 expedition. You'll get outfitted with fishing gear from pros who've been helping anglers for over 50 years. Afterward, you'll make your way through a maze of trails that take you to the lake, where you'll fish for salmon, perch, and trout.

01 Park Bait
02 Montrose Point Bird Sanctuary
03 Montrose Harbor (Fishing Spot)
ALBANY PARK

All Aboard to Albany Park

We're hopping on the Brown line for this guide to see what we'll find if we take it all the way to the last stop (Kimball).  Once you get off the train, you'll find yourselves in Albany Park, a neighborhood on Chicago's Northwest side that's a huge melting pot of various communities. Walk the neighborhood and you'll hear conversations in Tagalog, Spanish, Hindi, English, Urdu, Korean, Spanish, Bosnian, and tons of others being spoken. This guide gives us a small sample of this wonderful melting pot of a community where we can find classic Chicago hot dogs, a late night Mexican pastry shop, and coffee and cocktails all within a few blocks of each other. Here are the highlights.

01 Hot Dog Station
02 Nighthawk
03 Markellos Baking Company
LINCOLN PARK

A Hidden Picnic Spot Inside a Hidden Garden

We've got a relaxing picnic planned inside a garden, that in the words of Alfred Caldwell, was "planned as a sanctuary of the native landscape, a place sequestered from Megalopolis, the jungle of profound ugliness; a cool, refreshing, clear place of trees and stones and running water . . . a hidden garden of the people of Megalopolis." We scoped out a hidden spot inside this hidden garden and have you bringing Cuban sandwiches to complete our picnic setup.

01 Cafecito
02 Alfred Caldwell Lilly Pool
CHINATOWN

Midnight Madness

We're taking you on nighttime adventure in Chinatown where you'll grab drinks in a backroom cocktail bar and then you'll have a family style Cantonese feast. Here are the details.

01 Nine Bar
02 Kam Fung
OLD IRVING PARK

Over the River and Through the Woods

How far are you willing to travel for a hot dog? We’re here to figure that out. You’ll grab your bike and take it on the Metra all the way to Libertyville, IL. At that point, you’ll be closer to Wisconsin than Chicago. From there, you’ll go on an epic bike ride on a trail that takes you back towards the city and to one of the most iconic hot dog places in the Chicago area.

01 Grayland Metra station
02 Libertyville Metra Station
03 Des Plaines River Trailhead
04 Des Plaines River Trail (Cook County)
05 Gene's and Jude's
ROGERS PARK

Summer Sundays in Rogers Park

We've got a wholesome Sunday morning planned in Rogers Park. It starts at a small Korean-American breakfast diner run by Susie, the Korean grandma you've always wanted in your life. Afterwards, on the same block, you'll visit a Sunday farmers market that takes over a narrow cobblestone side street, and underneath a canopy of trees, you'll shop for fresh fruits, veggies, pies and cheese.

01 Susie's Noon Hour Grill
02 Glenwood Sunday Market
LAKEVIEW

Ready for a Really Crepe Time?

For this guide, we're combing good food, music, and board games all into one wonderful evening. You start at a 40+ year old French bistro for crepes, pate and frites, then head next door to an even older record store where you'll browse vinyl records, and finally, you'll spend the rest of the night with one of the largest collection of board games at your disposal. Here are the details.

01 La Creperie
02 Gramaphone
03 Bonus Round Game Cafe
WILLOW SPRINGS, IL

Summer Camping Season

This guide has you going deep inside a forest preserve where you'll camp along the shores of a small lake, do a bit of hiking, and hang by a campfire. With it being about 30 minutes from downtown Chicago, it's just about everything you need for a an easy weekend nature getaway.  

01 Camp Bullfrog Lake
02 Palos Trail System
WEST LOOP

A Little Bit of Work and A lot a Bit of Food

We've got a lazy Sunday in West Loop on the books. The day starts a local non-profit bookstore to dig through their collection of new and used books.  You'll then take that new novel you picked up and head a few blocks to a coffee house run in partnership with a world-renowned Japanese latte-artist. The day ends in the same place, because in addition to being a coffees house, it's also a bbq restaurant and ramen shop. Here are the highlights.

01 Open Books
02 Sawada
03 Green Street Smoked Meats / High Five Ramen

Drinks Are Just Around The Corner

There's a large residential section of Bucktown with an eclectic mix of historic greystones, two-flats, and multi-million dollar modern homes. It's the type of neighborhood you can have fun aimlessly wandering around daydreaming about which home is perfect for you. What makes this neighbor even better are the randomly scattered corner bars. For this guide, you'll visit three of these corner bars with three different vibes.

01 Leavitt Street Inn
02 The Charleston
03 Gallery Cabaret
CHINATOWN

A Culinary Tour Along the Red Line

We're taking the Red Line to go on a food expedition that starts in Chinatown and ends on the far North side in Little Saigon. We'll make a few stops along the way for some small and not-so-small eats. This is an especially good guide to follow with out-of-town friends/family to see and get a taste of Chicago's different neighborhoods in one go. We'll be munching on soup dumplings, donuts, chicken wings, and Vietnamese crepes on this culinary tour along the Red Line. Here are the details.

01 Hing Kee
02 Firecakes
03 Bird's Nest
04 Hai Yen Restaurant
RAVENSWOOD MANOR

Good Times Off the Brown Line

This guide has you exploring Chicago by train. You'll be visiting five different places off five different Brown Line stations. You'll start with pie, then hang out at a neighborhood bottle shop, and then make your way through a maze of floor-to-ceiling books. Afterwards, you'll end things with a choose-your-own-adventure option: either a combination dive bar/bowling alley or a 100+ year old movie theater.

01 First Slice
02 Rockwell Bottle Shop and Coffee
03 Ravenswood Used Books
04 Timber Lanes
05 Davis Theatre
BATAVIA, IL

A Bike Ride to a Physics Lab

About an hour outside of Chicago, there are thousands of scientists from all over the world working to answer fundamental questions about space, life, and our very own existence. Is time travel possible? Are we living in a multiverse? You know, all the things we think about right before bed. This guide has you driving out to Batavia, IL where you'll be visiting a particle accelerator and physics laboratory that's housed on on a 6,800 acre site. You'll be touring exhibits, learning about neutrinos, and biking all across the site. Here are the details.

01 Lake Law
02 Margaret Pearson Interpretive Trail
03 Wilson Hall

Next Stop: World Class Gardens and Live Theatre

This is part of our “Known / Unknown” series. For each guide in this series, we pair a classic, essential landmark with an overlooked place nearby. Today we’re going to take the Metra train to the North Shore where you'll a relaxing morning having a picnic and stroll through a 385 acre garden. That's followed by a live theatre performance in a nationally recognized venue nearby. Here are the highlights.

01 Chicago Botanic Garden
02 The Writer's Theatre
GARFIELD PARK

A Winter Garden and Kitchen

This week's guide takes you to Garfield Park in search of a bit of inspiration. The first stop is to one of the oldest and largest conservatories in the country, where you'll wander through 4.5 acres of indoor gardens and let the vast rooms of tropical plants and small ponds help you de-stress. Afterward, you'll visit a restaurant with a socially conscious mission of supporting men and women to overcome poverty and homelessness. Here are the highlights. 

01 Garfield Park Conservatory
02 Inspiration Kitchens
UKRAINIAN VILLAGE

It’s A Privilege to Visit Ukrainian Village

Chicago's history has been shaped by different waves of immigrants from all over the world, and we're celebrating part of that history with a visit to Chicago's Ukrainian Village neighborhood. This neighborhood has been a central hub for Ukrainian-American's since the first mass migration of immigrants in 1870.  Our trip to has us taking in Ukrainian food, art, and history on this three-stop guide.  Here are the highlights.

01 Ukrainian Institute of Modern Art
02 Tryzub Ukrainian Kitchen
03 Ukrainian National Museum
HUMBOLDT PARK

Lola from Humboldt Says Hi

This guide has you going on a classic neighborhood walkabout around Humboldt Park. It starts with a Coney Island hot dog at a corner hot dog shack. You'll then head to an occult bookstore for a tarot reading session. Afterward, you're breaking for apple pie at a throwback diner with some strong 1950s vibes. More shopping follows at a feminist-inspired gift shop. We end things at a neighborhood cocktail bar with a mix of art deco and modern Southwest design flair.

01 Lola's Coney Island
02 Space Oddities
03 Spinning J Bakery
04 Humboldt House
05 The Hi-Lo
ANDERSONVILLE

Super Swede Sunday

This guide takes you on a mini Swedish adventure in Andersonville that works great as a chill Sunday afternoon outing. This is a historically Swedish neighborhood on Chicago's Far North Side, and we'll be doing our best to immerse ourselves into the food and culture. Here are the highlights.

01 Svea
02 Swedish American Museum
03 Simon's Tavern
ROGERS PARK

Rogers Park in the Dark

In Rogers Park, there's a narrow cobblestone street full of shops and bars that feels more like old world Europe than it does Chicago. This guide has you spending the evening there drinking hot cocktails, playing old school arcade games, and catching a live jazz performance to cap off the night. Here are the details.

01 Rogers Park Social
02 Mission Control
03 Le Piano
LONG GROVE, IL

A Suburban Day Trip

This guide has us venturing out into the deep dark abyss, a terrifying hellscape for 20-somethings living in the city. That's right, we're headed to the Chicago suburbs. While it gets a bad rap, we've got a day trip planned that might have you feeling different by the end of it. You'll make your way to Long Grove, IL, about a 40 minute drive northwest of Chicago. It's home to a small downtown with rural farming charm. You'll walk through cobblestone sidewalks, munch on apple cider donuts, rummage through antiques, and have a beer in the woods.

01 Long Grove Coffee Co.
02 Epilogue Arts
03 Corked Wine Bar
04 Joanie's Pizzeria
05 Covered Bridge Creamery
06 Buffalo Creek Brewing
07 Long Grove Confectionary Co.
EVANSTON

Night Sky Watching

We visit the past and peer into the future all in one guide. You'll make your way to Evanston to visit Northwestern University. It starts with a tour of an art and history museum, and then you'll follow up with an astronomy lesson inside an open-air observatory. Between those stops, you'll grab a bite to eat at a chicken joint popular with students and locals alike. Here are the details. *Logistics note - This guide, in its entirety, is only good for Friday night as the observatory is only open to the public on Friday evenings.

01 The Block Museum
02 10q Chicken
03 Dearborn Observatory
LINCOLN PARK

Garden to the Grave

This guide is part of our "Known/Unknown" series where we pair an essential Chicago landmark with some more obscure spots nearby. It starts with a leisurely bike ride down the Lakefront Trail where you'll visit a prairie-style garden with iconic views of the Chicago skyline (the "Known"). Afterwards you'll continue on with a peaceful and quiet bike tour through a 121 acre cemetery that's home to the final resting place of famous Chicagoans like Ernie Banks, Jack Johnson, George Pullman, and Louis Sullivan ("the Unknown"). Here are the details.

01 Nature Boardwalk
02 Graceland Cemetery
UPTOWN

Getting Down in Uptown

Friday and Saturday nights tend to get all the glory, so we’re going to show Thursday night some love and paint the Uptown drinks, and dancing. Why Thursday? First of all, why not? But more importantly, it’s the only night of the week that Alan Gresik’s Swing Shift Orchestra plays at The Green Mill. You'll start with cocktails in the apartment lobby for craft cocktails and then make your way down the block for more drinks, live music, and dancing.

01 Larry's
02 Green Mill Lounge
HYDE PARK

Island Hikes in Hyde Park

This guide has you strolling through fields of wild flowers and exploring an island nature preserve on the South Side. But before that, you'll grab brunch and beignets at a French cafe and then head down the block to a basement bookshop where you'll grab a book to take along our nature walk. Here are the details.

01 Plein Air Cafe
02 57th Street Books
03 Bobolink Meadow
GOLD COAST

Italian Eats and Cuban Drinks

Walking through Chicago's Gold Coast neighborhood is the like the real life version of scrolling through Zillow and daydreaming about the type of place you'd buy once that dogecoin investment comes through. It's dotted with historic mansions and beautiful row homes that make this not only the most expensive neighborhood in Chicago, but also the seventh richest urban neighborhood in the United States. While you can expect to find the usual clusters of high end retail stores, fashion brands, and fine dining options, we've got other plans in mind. For this guide we've got a classic date night that starts at a small, intimate Italian restaurant for shared plates of burrata. Afterwards, you'll head down the street to a 1940's, Cuban-inspired cocktail bar to end the night.

01 Eduardo's Enoteca
02 Sparrow
BRIDGEPORT

A Six Pac(zki) of Beer

This guide takes us to Chicago's Bridgeport neighborhood, where we'll spend the afternoon doing a reverse progressive lunch. We start with dessert and scarfing down a paczki or two; we then grab some tavern-style pizza at an old-school neighborhood pizza place, and then we finish things off in a converted industrial space turned brewery.

01 Bridgeport Bakery
02 Phil's Pizza
03 Marz Community Brewing
WEST TOWN

Can You Dig It?

Puck rock culture in the 1970s ushered in Chicago's DIY (do-it-yourself) scene. It was a movement led by artists and musicians who wanted to circumvent mainstream music labels and venues, and instead, put on their own DIY shows in unsanctioned warehouses, basements, and homes. For this guide, we're going to get an introduction into this scene. You'll be taking in a live music performance at an artists loft in West Town that by day is a ceramics studio and by night is transformed into a DIY music space. Before that, however, you'll be getting a pre-show cocktail at a small batch distillery nearby.

01 Rhine Hall Distillery
02 The Digs Chicago
ROGERS PARK

Beaches and Cream

During the summer, Rogers Park can feel like a mini-beach town if you know the right spots to visit. For this guide, we've got an afternoon beach trip all planned out. You'll start at a beach side cafe for slushies and then walk 10 feet to find a spot on the sand. Once you've got enough sun and beach, you'll make your way through a quiet lakeside residential neighborhood until you come upon a small enclave of shops and cafes that give off strong small town beach vibes. You'll end the day there with a post-beach meal of ice cream, sandwiches, and coffee.

01 Ropa Cabana
02 Charmers Cafe
CHINATOWN

From Downtown to Chinatown

This guide has us visiting Chinatown but we won't be getting there by car, train, bus, or bike. In fact, for our mode of transportation, we won't need roads. We'll be taking the water taxi to Chinatown for some deluxe dim sum. Here are the highlights.

01 Water Taxi
02 Triple Crown
03 Ping Tom Memorial Park
AVONDALE

An Avondale Afternoon

This guide has you spending your afternoon in Logan Square and Avondale. It starts with you feasting on elevated bar food in a quiet residential corner bar. Afterwards, you'll visit the second floor of a building that was left vacant for decades, but has found new life as a vintage bowling alley. Finally, you'll end the day at a nearby bar and performance venue for comedians, dj sets, or live jam sessions.

01 Small Bar
02 Avondale Bowl
03 Sleeping Village
LAKEVIEW

Water You Up To This Weekend?

There's been a big flurry of development along the Chicago River over the past few years. A lot of the attention has been on downtown's river walk and future mega developments like Lincoln Yards, but there's a whole host of smaller projects popping up along the river. For this guide, we're visiting a few outdoors spots that are taking advantage of their proximity to the North Branch of the Chicago River and we'll get on the water ourselves. Here are the details.

01 Hexe Coffee
02 Riverwalk
03 Rockwell on the River
HUMBOLDT PARK

Dive into the Weekend

Every neighborhood has that one classic Chicago corner bar that everyone loves. For this guide, we're visiting three neighborhoods and their corner dives for an epic night of cheap drinks, pool, and good times. Here are the details.

01 Archie's Tavern
02 Inner Town Pub
03 Chipp Inn
WOODLAWN

Summer Markets on the South Side

There are no shortage of outdoor markets when summer rolls around, and for today's guide we'll be visiting two staples on the the South Side. You'll first head to a summer farmer's market in Woodlawn, just south of the University of Chicago campus, where we'll pick up fresh produce, pies, and a smorgasbord of items from a local French chef. Afterwards, we continue our quest for good food at a mini outdoor market constructed from repurposed shipping containers. Here are the details.

01 61st Street Farmer's Market
02 Boxville
WEST LOOP

For Good(ness) Sake

When most folks think of Japanese cuisine, they think of either sushi or hibachi. This guide features neither. Instead, we start this guide with Osakan street food and a rich bowl of tori paitan ramen. From there, you'll take a quick walk around the block for an order Kakigōri, a Japanese shaved iced, for dessert. We finish the night up with drinks at an underground saké bar. Here are the details.

01 Ramen Takeya
02 Gaijin
03 Booze Box
LAKEVIEW

Haunted Pub and a Magic Show

We’ve got a full night of paranormal haunts and magic. It starts at a classic English pub in the heart of Lakeview, where the ghost of a young woman is sometimes said to have trapped people inside. After munching on haunted fish and chips and throwing back a few pints, you'll head to a close-up magic show in a small storefront theater. Here are the details.

01 Red Lion Pub
02 Trickery
ROSCOE VILLAGE

Do You Know, About Antiques Row?

Twenty-five years ago, on the southern end of the Roscoe Village neighborhood, an eight-block stretch of Belmont Avenue was home to 'Antiques Row.' At its peak, upwards of 30 antique shops and resale markets clustered along this one-mile corridor. Nearly every other shop was an antique shop. The scene then was like a bustling flea market with vintage furniture and knick-knacks pouring out the door and onto the sidewalk. But nothing lasts forever; shops closed or moved one by one, and today there are only a few left standing. You're visiting three antique shops that continue the legacy of Antiques Row, and afterward, we make our way to a local tavern to take stock of our shopping haul. Here are the details.

01 Good Old Days Antiques
02 Father Time Antiques
03 The Lazy Dog Antiques
04 Four Moon Tavern
LAKEVIEW

Game On

For this guide, we're combining good food, board games, and cupcakes all into one wonderful evening in Lakeview. We start at a family-owned Mexican restaurant that has been serving some of the best mole the city has to offer, we then head down the street to spend the evening with one of the largest collection of board games at our disposal. We end the night at a late-night bakery run by a former contestant on Netflix baking competition show, Sugar Rush.

01 Buena Vista
02 Bonus Round Game Cafe
03 Jennivee's Bakery
MADISON, WI

500 Foot Bluffs and a Hillside Winery

We're hitting the road for a weekend trip to Wisconsin. It starts with a 2.5-hour drive to Madison, Wisconsin, our home base for the weekend. After getting settled, the next part of the trip takes us less than an hour away for some serious hiking up a 500-foot bluff. After a day of climbing boulders and hiking through woods, we reward ourselves with cheese and a bottle of wine on the hillside of a nearby vineyard.

01 Madison, WI
02 Devil's Lake State Park
03 Wollersheim Winery and Distillery
LOGAN SQUARE

Pottery, Beer, and Burgers After Dark

The night starts and ends in Logan Square. We kick things off with a 3-hour wheel throwing workshop at pottery studio . We then decompress with your choice of 48 beers, wines, and ciders in a self-serve taproom. Things end the way any great night in Chicago ends -- eating burgers and fries underneath train tracks at midnight. Here are the details.

01 Penguin Foot Pottery
02 Navigator Taproom
03 Redhot Ranch
BRIDGEPORT

Rock With Me

We're hanging out in Bridgeport and going on a classic neighborhood walkabout. It starts off with coffee at a beloved neighborhood cafe, and then you'll cut across three residential blocks to visit a public art exhibit and gallery. You'll then walk along one of the Bridgeport's main thoroughfares to grab a 3lb burrito at a corner super market. Things end at a rock quarry turned park with spectacular views of downtown.

01 Jackalope Coffee and Teahouse
02 Co-Prosperity Sphere
03 Martinez Supermercado
04 Henry C. Palmisano Nature Park
SOUTH LOOP

Let Them Eat Cake, Steak, and Have a Beer Break

This guide requires you to start with an empty stomach, because you'll be merrily strolling through South Loop and the Near South Side, eating and drinking more than you ever need. It starts at a classic Chicago diner serving deep-dish pizzas, Italian lemonade, and a famous breaded steak sandwich. You'll then make your way to a local brewery for a chocolate cake and beer pairing to finish things off.

01 Ricobene's
02 Moody Tongue
UPTOWN

Eat, Climb, Love

We've got a classic daytime date on the docket. We're hanging out in Uptown and ease into things at a rustic coffee shop for some good conversation over an ubae latte. Afterwards, you'll head down the street to a former bank whose second floor has been turned into a bouldering gym. Finally, if the date is still going well, the last stop is a post-gym meal at a Vietnamese restaurant where we're going to try something other than pho. Here are the details.

01 First Sip Cafe
02 First Ascent
03 DaNang Kitchen
RIVER WEST

The Inside Scoop on Outsider Art

If there was a word to describe this guide, it would be "appreciation." We're spending the afternoon at a museum that, for the past three decades, has allowed visitors to appreciate works from self-taught artists outside of the mainstream art community. In many cases, these artists often lived with mental illness or had other circumstances that kept them from pursuing a more traditional art career. Afterwards, we keep the on the same theme and head to a nearby nondescript bodega in the middle of a residential neighborhood. There's so much more to this bodega than meets the eye and we step inside to find out what makes this place special.

01 Intuit: Center for Intuitive and Outsider Art
02 Taqueria El Jardin
DOWNTOWN

The Island Downtown

Being in the middle of the city doesn't mean we have to give up on enjoying green space. We're spending the day at Northerly Island, a former airplane landing strip that's been transformed into a 119 acre nature preserve with views of Downtown Chicago you won't get anywhere else. This is our second time here, after featuring it a few years ago, and we've got lots to update you on. Here's the agenda for this guide.

01 Northerly Island Parking Lot
02 Lookout #1
03 Lookout #2
LAKEVIEW

You’re in for a Crepe Time

This week's guide get's us out of the house for a quick mental health recharge. We're headed to Lincoln Park where we start the day munching on crepes and sipping lattes before spending the next hour in a pet bunny cuddle therapy session. Here are the details.

01 The Crepe Shop
02 Cuddle Bunny
ELK GROVE VILLAGE, IL

Where The Elk Should We Go Today?

For many of us Chicagoans, wintertime means hibernating inside, curled under a heavy blanket, and waiting for the worst of winter to pass.  Well for this guide, we won't be hiding from mother nature -- instead we'll be venturing outside for a winter weather hike and seeing for ourselves how beautiful this season can be.  Head to the Northwest suburbs to visit a small herd of elk at an elk pasture, and then take a peaceful hike through the woods. Here are the details.

01 Busse Forest Elk Pasture
02 Busse Woods Trail Head
SOUTH SHORE

The Great Wall of Chicago

We're taking a trip to Chicago's South Shore where we'll be visiting a monstrous relic from an abandoned steel complex. This once busy industrial complex is now a quiet park that runs along the shores of  Lake Michigan, but after the park conversion, the city left behind a series of 30 feet high concrete walls that span over 5.5 football fields. We're here to explore these walls and see what's on the other side.

01 Steelworkers Park
02 Ore Walls
PILSEN

Pilsen by Car

This week’s socially distanced guide will let you enjoy that classic dinner and a movie date all from the comfort of your car. We will be driving down to Pilsen to enjoy some delicious Mexican food, sample artisan chocolates, and finish the night with a movie at the local drive-in.

01 5 Rabinitos
02 Chocolat Uzma
03 ChiTown Movies Drive-In
PALOS TOWNSHIP, IL

Take a Step Outside

Put on your hiking shoes because you're visiting a former toboggan hill converted into an outdoor fitness center in the woods. Afterward, you'll set off on a quiet hike atop a 100 ft bluff that extends over 8 miles. The afternoon ends at a nearby nature center to visit owls, falcons, and amphibians. Here are the details.

01 Swallow Cliff Woods
02 Little Red Schoolhouse Nature Center
SAWYER, MICHIGAN

Pick Apples and Hike Monstrous Dunes

Pack the car because you're going on a day trip to Southwest Michigan. It's close to a 2-hour drive, and if you're going during the right time of year, you'll start at a pick-your-own peach/grape/apple orchard on a hillside farm. Afterward, you'll head to a park covering nearly 2,000 acres and 6 miles of sandy trails that go up and over steep sand dunes. The day ends at small downtown in one of the many communities dotting Lake Michigan's coastline.

01 The Shafer Farm
02 Warren Dunes State Park
03 Greenbush Brewing
LOCKPORT, IL

A Lunch Course Followed By A Golf Course

Put on a comfy pair of walking shoes and bring your appetite because you're venturing out on a day trip to Lockport, Illinois. You'll start the day with some vegan eats and then head to the #5 ranked disc golf course in the world. It's set in the woods between steep dolomite cliffs and ancient ravines. Here are the details.

01 The Vegan Cafe
02 Dellwood Disc Golf
03 Canyons Disc Golf
LITTLE VILLAGE

Cafecitos and Cocteles

This guide takes us to Chicago’s Southwest side. We’ll be exploring Little Village, or La Villita as the locals know it. Considered to be one of the city’s largest and most cherished Mexican-American communities, we’ll be getting a small taste of some of the local favorites, along with a peek into a newer establishment that is proud to call this neighborhood home. Here are the details.

01 Little Village Arch
02 La Cathedral Cafe & Restaurant
03 Day of the Dead Mural
04 Art by Jay Jasso
05 Mural by Mr. Pintamuro
06 Osito's Tap
07 El Nopal Bakery
NORTH PARK

Early Breakfast, Early Hike

This guide takes us to Chicago's Northwest side. We're going to spend the morning hiking through a beautifully preserved nature center with trails covering 46 acres of woodland, wetland, prairie, and savanna. But before any successful hike, we start with a meal. Today, that means Korean pajeon pancakes and bread pudding french toast at a nearby breakfast spot. Here are the details.

01 Bryn Mawr Breakfast Club
02 North Park Village Nature Center
UKRAINIAN VILLAGE

Back Alleys and Back Yards

For this guide, we're keeping it low-key and spending the afternoon in Ukrainian Village for a Sunday Funday. You'll start the afternoon at a tiny, back alley pizza joint, but with seating at a premium, you'll head down the street to a backyard bar that we all wish we had at our own home. The rest of the afternoon is spent there scarfing down pizza and sipping on house cocktails.

01 Pizza Friendly Pizza
02 Sportsman's Club
SOUTH SHORE

A South Shore Palace

Travel south along the Lakefront Trail and you'll eventually reach the entrance to a South Side palace. Sitting on over 70 acres, this public space, dubbed "a palace for the people," is the focus of this guide. We'll visit a historical landmark and take a stroll through a nature reserve where we uncover stone fire pits overlooking Lake Michigan.

01 South Shore Cultural Center
02 South Lawn / Beach
03 South Shore Nature Santuary
BROOKFIELD, IL

That Other Zoo

We're headed about 45 minutes from Chicago to visit that other nationally recognized zoo in the Greater Chicago area. This is a particularly good guide for those days where you want to spend the afternoon out of the city, but don't want to make too much of a hassle out of it. Here are the highlights:

01 Union Station
02 Brookfield Zoo
ZION, IL

Lakefront Camping

For this guide we’re off to Illinois State Beach Park where we’ll be camping right off the coast of Lake Michigan. Here are the highlights in this guide.

01 The Campsite
02 Piggly Wiggly
03 Illinois Beach Nature Reserve
CHATHAM

Jahmal Cole | Chatham

We're headed to Chatham on Chicago's South Side. For this guide, we met up with Jahmal Cole, founder of My Block, My Hood, My City, a Chicago non-profit organization that works with students from under resourced communities, and takes them on city explorations throughout Chicago. He takes us around his neighborhood to grab giant donuts, have a plate of chicken and waffles, and tell his story.

01 Captain's Hard Times Dining
02 Brick Bungalows
03 Dat Donut
SAUGANASH

Into Labagh Woods

While stay at home orders are in full force, one thing we're still allowed to do is visit the surrounding forest preserves while practicing physical distancing. For some time outside of the home, head to this nearby Northside trail and explore Labagh Woods and the railroad track turned trail that runs through it.

01 Weber Spur Trail
02 Labagh Woods
HYDE PARK

Find Hyde Park

This guide takes us to the heart of Hyde Park where we'll start the day with breakfast at President Obama's favorite diner. We'll then take a short stroll through the neighborhood and stop by a few interesting places nearby.  Finally, we finish the day with a some much needed quiet time in a tranquil Japanese garden that feels like an oasis in the middle of the city.  Here are the highlights.

01 Valois Restaurant
02 Harper Theater
03 Osaka Garden
THE LOOP

A Downtown Architecture Walk

No matter how long you've been in Chicago, the city's skyline and its architecture will always find a way to stop you in your tracks in a daze of wonderment. Maybe it happens during "Chicago Henge, " the twice a year phenomena where the sun sets in perfect alignment with downtown's grid patterned streets. Or perhaps it's during your daily commute on the Brown line when the train crosses the bridge over the Chicago river. For this guide, we’ll try to replicate some of those awe inspiring moments on a downtown tour where we’ll see the city from high above and walk down the halls of historic buildings. Here are the details.

01 Cook County Law Library
02 The Rookery
03 Federal Reserve Money Museum
04 Monadnock Building
05 Harold Washington Library
PULLMAN

A Neighborhood Turned National Monument

For this guide we're headed all the way to 112th street on Chicago's South side where we'll tour a historic neighborhood and learn a little bit about one of the nation's first planned industrial communities.  While we're down this way, we're also going to visit a nearby smokehouse down by the river. Here are the highlights.

01 Calumet Fisheries
02 Pullman Historic District
EDGEWATER

Roaming Through Rosehill

Cemeteries aren’t all headstones and hauntings… okay, so there are a lot of headstones. But many of them are incredible works of art. So today, you'll be taking a stroll through Rosehill Cemetery. You'll be entering the cemetery through the Ravenswood gate at Rosehill Drive and Ravenswood Avenue, then making three main stops within the cemetery itself.

01 The Civil War Memorial
02 The Grave of Frances M. Pearce
03 The Rosehill Mausoleum
LOGAN SQUARE

A Church Turned Circus

On the first Saturday of every month, there's a former church, turned circus training and performance center, that opens up its doors for a show. For this guide, we're headed to that church located in Logan Square to watch circus performers fly through the air, walk on tight ropes, and perform other incredible physical feats. But before show, we're going to take advantage of our time in the neighborhood to dine on traditional Puerto Rican cuisine. Here are the highlights:

01 La Bomba Restaurant
02 Aloft Circus Arts
OAK PARK

Wright This Way

We're going to head to Oak Park to visit the home of the greatest American architect to have ever lived. From downtown, we're hopping on the CTA Green line for a short 30 minute ride to Oak Park where we'll be dropped off near the Frank Lloyd Wright–Prairie School of Architecture Historic District. This historic district, which covers a large chunk of downtown Oak Park and the surrounding residential areas, contains the largest collection of Frank Lloyd Wright designed buildings in the world. There's no way to see everything in one trip but you can follow along this introductory guide to get you started. Here are the details.

01 Frank Lloyd Wright Home and Studio
02 Jerusalem Cafe Restaurant
03 Pleasant Home (and Mills Park)
04 Unity Temple
LITTLE ITALY

Not So Little Italy

For this week's guide, we're headed to Little Italy on Chicago's Southwest side, and exploring it two different ways. It's kind of like a 'pick-your-adventure' type guide where you can choose to either dine on a plate of chicken picante at a classic Italian eatery and finish off at an Italian ice stand, or grab some picnic provisions at an Italian grocer and have lunch in a nearby park under the city skyline. Here are the details.

01 Tufano's Vernon Park Tap
02 Mario's Italian Lemonade
03 Conti Di Savoia
04 Arrigo Park
HUMBOLDT PARK

Big Fish in a Small Pond

For this guide, grab the fishing pole and tackle box from storage, because we'll be relaxing by a lagoon and doing some fishing in Humboldt Park. Afterwards, we're going to stroll through this 219 acre park, which is also home to a vibrant Puerto Rican community, and end the day at a mom and pop diner for an authentic Puerto Rican lunch. Here are the details.

01 Humboldt Park Boathouse
02 Diana's Restaurant
GENEVA, IL

Geneva, IL

We're headed on an adventure to small town America just 40 miles west of Chicago. On this guide we're hopping on the Metra to Geneva, IL and starting the day off with breakfast brought to you by a world-renowned pastry chef, then we make our way through a massive row of boutique stores and antique shops. That's followed by a stroll through a Japanese garden and we end the day at a local brewery. Here are the highlights.

01 All Chocolate Kitchen
02 3rd Street
03 Fabyan Forest Preserve
04 Penrose Brewing Company
KENWOOD

Lake Michigan’s Coral Reef

Here's a fun fact for this guide. About 425 million years ago, Chicago was actually located south of the equator in a tropical sea. You can see evidence of that in small pocket of Lake Michigan where the compressed remnants of a coral reef still sit today. It's an area that is teeming with underwater life, and we'll be grabbing our snorkel gear and exploring it with this guide. After we step out of the water, we'll end our outdoor adventure exploring a quiet bird sanctuary tucked back into a small corner off Lakeshore Drive. Here are the details:

01 Morgan Shoal and Silver Spray Shipwreck
02 Burnham Nature Park
GLENCOE, IL

A Dog Day Afternoon

For all you dog owners, you know that sinking feeling you get as you hear your dog whimpering while you walk out of the house.  Well, for this guide, we're not leaving your best pal behind. In fact, we're taking them on an adventure around the city. We start by kayaking through an 894 acre forest preserve with your dog at the helm of the kayak. We then make our way back into the city for cocktails, whiskey, and a backyard bbq at a dog friendly bar. Lastly, we end the day with an ice cream for you and an ice cream for your good boy/girl.  Here are the details.

01 Skokie Lagoons
02 Ludlow Liquors
03 Pretty Cool
OAK FOREST, IL

From the Office to a Campsite in 45 Minutes

There's something about pitching a tent and sitting around a campfire to make us forget about our worries. For Chicagoans, a camping trip normally means driving over an hour outside of the city into Michigan or Wisconsin. While those types of trips can be great, they also can be a hassle to plan out when all you're looking for is a quick retreat from the city.  This guide is for those times when you're looking for an easy overnight getaway, and you're looking to leave now. We'll be camping at one of Cook County's forest preserves to do a bit of hiking, grilling, and star gazing. If coming from downtown Chicago, you can be out the door to having a camp site set up in about 45 minutes.  *Here's another important note. If I had to rate the camping difficulty level on a 1 to 10 scale, where 1 is backyard camping at your parent's house, then this is a 2.

01 Camp Sullivan
02 The Tent Camping Sites
03 Trails and Night Hikes
BRIDGEPORT

Bridgeport Has Got a Bit of Seoul

We're headed to Chicago's Southwest side, and spending the evening feasting on a mashup menu of Korean-inspired Polish food. We'll then walk down the street to visit an experimental cultural center that hosts a broad array of  events like festivals, performance art, comedy shows, and art exhibits.  Here are the details.

01 Kimski
02 Co-Prosperity Sphere
THE LOOP

Fine Art and Fine Tea

This guide is all about to getting cultured. We start in the Loop at a Russian tea house to talk current events while sipping tea and snacking on a literal tower of savory snacks. Afterwards, we'll walk down the street to tour an historic artist enclave that houses 10 floors of art studios, music halls, and a handful of shops. Here are the details.

01 Russian Tea Time
02 Fine Arts Building
BEVERLY

Where Should We Mead Up?

A while back we took advantage of the Metra train's $8 all-you-can ride weekend pass and visited a forest preserve on Chicago's far North side. We're following that up with another trip, but this time we're taking the Metra the opposite way to drink mead, wine, and beer on this drinking tour.

01 Wild Blossom Meadery
02 Hailstorm Brewing Co.
03 Soundgrowler Brewing
LOGAN SQUARE

A Whisky Proposition

This guide is for the whisky connoisseurs out there. We're visiting a back room bar to peruse a list of over 400 whiskys and afterwards we head five minutes away for another round of rare spirits. But before all that, we've got to properly prepare ourselves by feasting on Asian versions of cheeseburgers and Italian beef sandwiches. Here are the details.

01 Bixi Beer
02 Longman and Eagle
03 Billy Sunday
ANDERSONVILLE

A Magical Adventure in Andersonville

Andersonville is, without a doubt, one of Chicago’s most personality-filled neighborhoods. From its Swedish heritage to its catering towards the LGBTQ+ community, many people find it to be a great, community-oriented place to call home or turn into a regular hangout. It also houses a few spots unlike anywhere else in the city. The journey to this Northside neighborhood is filled with taxidermy, magic (literally), and  good drinks.

01 Woolly Mammoth
02 Chicago Magic Lounge
03 Simon's Tavern
LAKEVIEW

Dance Off Those Late Night Cupcakes

This guide has us in Lakeview and starts off with a nice wholesome evening of Korean fried chicken and cupcakes. Our wholesome night starts to take a turn when we make to a karaoke bar just down the street. With our night time debauchery fully underway, we end the evening at a basement dance club where we'll be kicking back cheap drinks to 90s/00s hip-hop. Here are the details.

01 Crisp
02 Molly's Cupcake
03 Trader Todd's
04 Baby Atlas
LEMONT, IL

Temples and Waterfalls

We're taking a short trip outside the city to hike through a 2,500 acre forest preserve. We start by grabbing coffee at a quirky and retro coffee house, then we head to the trail head where we'll hike through rolling hills, waterfalls, and overlooks. We'll then take a detour off the trail to have lunch beneath a Hindu temple. Here are the details.

01 Ashbary Coffee House
02 Waterfall Glen Forest Preserve
03 The Hindu Temple of Greater Chicago
JEFFERSON PARK

A Wheelie Fun Bike Ride To The Lagoons

For this guide, we're taking out the bikes and doing some heavy duty pedaling across Chicago. We're headed to the North Branch Trail, and we'll go 21 miles (one-way) to the Skokie Lagoons.  This guide documents the notable spots along the way. Here are the highlights.

01 Forest Glen Woods
02 Historic Wagner Farm
03 Willow Road Dam
04 Skokie Lagoons (Forest Way Picnic Grove)
INDIANA

The Big Bad Dunes

For this guide, we're headed about an hour away and crossing over to Indiana where we we'll be hiking through sand dunes and some of the most beautiful trails you'll find near Chicago. Right along the Southern tip of Lake Michigan is the Indiana Dunes State Park and surrounding it is the Indiana Dunes National Park. We'll be checking out a bit of both for this guide. Let's get started with the highlights.

01 Dune Park Station
02 Mount Jackson
03 Beach House Blowout
04 Walk-in Campsites
OGLESBY, IL

A Short Day Trip To Canyons, Waterfalls, and Crawfish

For this guide we’re heading 1.5 hours out of Chicago for an easy day trip exploring  canyons, waterfalls, and indulging in cajun cuisine. Here are the highlights in this guide.

01 Cajun Connection
02 Starved Rock State Park
03 Downtown Utica
LINCOLN PARK

Hand Me A Golf Club and Yummy Grub

When life gets busy and stressful, sometimes we just need to take a moment to swing and hit stuff really hard. Well, that's what we'll be doing with this guide as we make our way to a driving range in the heart of Chicago. We then follow up with comfort food. Here are the details.

01 Diversey Driving Range
02 Del Seoul
03 Molly's Cupcake
WEST TOWN

Brunch, Beers, and A Little Black Dress

A good neighborhood is one that can offer entertainment and good hangs at any time of day. We love West Town for that. Its nightlife scene continues to build and bustle, but the streets definitely aren’t dead before the sun sets. We filled a recent Sunday with brunch, beer drinking and shopping along Chicago Avenue. It’s the perfect “Sunday Funday” to replicate if you’re looking to have a great time, but still be home by 4 p.m.

01 Flo
02 Seek Vintage
03 Forbidden Root
PILSEN

What’s New Pilsen?

We're headed to Pilsen for this guide and doing a neighborhood walkabout to catch some of the sights and sounds of the area. The neighborhood is constantly changing and if you haven't been here in awhile, then you'll probably find something new the next time you visit. On the docket today is a Vietnamese coffee, a community bookshop, a local artist shop, a massive plate of deep-fried carnitas, and finally some churros to end the day. Here are the details.

01 Ca Phe Da
02 Pilsen Community Book Shop
03 Pilsen Outpost
04 Carnitas Uruapan
05 Xurro
LINCOLN PARK

Deep Thoughts and Deep Dish

Sometimes the gray and wet Chicago winters can put us in a funk. We don't want to go anywhere, and weekend plans consist of bundling up at home with something hot to drink and eat. After consecutive weeks of that, you might get a little stir-crazy. We're going to change that by getting out of the house and heading to a cozy book store/bar/ice cream in Lincoln Park. Take it over and make this hang out space your winter home.

01 Kibbitznest
02 Pequod's
GOLD COAST

Going Under the Knife

For this week's guide we're adding another edition to our Known/Unknown series where we pair a classic, essential landmark with an overlooked place nearby. We start off at our "Known" location, the Museum of Contemporary Art where we'll be touring 4 floors of galleries and a new outdoor courtyard that doubles as a nice picnic spot. We then grab lunch inside a place that's housed in what basically looks like a giant mansion. Finally, we head to our "Unknown" location, a museum dedicated to the history of medicine and science. Here are the details.

01 Museum of Contemporary Art
02 Restoration Hardware
03 International Museum of Surgical Science
HYDE PARK

Art is Good for the Soul…Food

We're spending the day getting cultured on a museum crawl on the South Side. We'll be visiting a fine arts museum on the University of Chicago's campus, then over to an independent museum dedicated to African American culture and history. Afterwards, we're walking up a tower to get a birds-eye view of Hyde Park, and finally we do what we do best -- eat some soul food. Here are the details.

01 Smart Museum
02 Dusable Museum
03 Logan Center for the Arts
04 Daley's
MICHIGAN

A Michigan Road Trip: Part II

Welcome to Part II of our Michigan Road Trip guide. Last week we stopped by Saugatuck, Michigan for some boating, hiking, and beach time. For Part II, we're headed about 25 minutes north of Saugatuck to Holland, Michigan where we'll be combining loads of eating with some outdoor escapades. Here are the highlights.

01 Downtown Holland
02 Holland State Park
03 Mount Pisgah
MICHIGAN

A Michigan Road Trip: Part I

We're hitting the road with this guide and heading east to visit our neighbors and friends in Michigan. There are a number of summer vacation towns along Lake Michigan, and we're highlighting a few that make for an action packed weekend trip. In fact, we were so productive that we're splitting this guide up into two parts. For this week's guide we're taking you to Saugatuck where we'll be doing a bit of boating, swimming, hiking, and eating.   Here are the highlights of the Saugatuck guide.

01 Retro Boat Rentals
02 Downtown Saugatuck
MILWAUKEE, WI

A Milwaukee Weekender

For this week’s guide, we’re taking you on an overnight trip to that other big city on Lake Michigan. I’m talking about Milwaukee, which is a real easy 1.5 hour Amtrak ride from Chicago’s Union Station. We met up with a local who served as our tour guide, and provided us with a action-packed 24+ hours in Milwaukee. Here are the details.

01 Great Lakes Distillery
02 Lost Valley Cider Co.
03 Indulgence Chocolatiers
04 Riverwalk
05 Milwaukee Ale House
06 Victoria's On Potter
07 Boone and Crockett
08 Milwaukee Public Market
09 Bublr Bike
THE LOOP

Bean There Done That

We've got another guide to add to our Known/Unknown series where we pair an essential Chicago landmark with overlooked places nearby. Today we're on an early morning trek to one of the most recognizable landmarks in downtown Chicago, then head across the street to visit a century old free museum, and finally eat breakfast at an old school diner. Here are the highlights.

01 The Bean
02 Chicago Cultural Center
03 Pittsfield Cafe
WILMETTE

On the Northshore

This is a guide when the weather is warm you're in the mood to grill food by the lake, throw the old pig skin around, and picnic in the grass.  To start, we'll be going as far North as you can go on the red/purple line train to get to the North suburb of Wilmette. What makes this particular park worth going to? Well, overlooking the park is a massive and uniquely designed temple which makes the backdrop while you're picnicking different than any other experience you'll get in Chicago. We'll also have a chance to visit the temple and learn more about it. Here are the details.

01 Gillson Park
02 Bahai Temple
BRONZEVILLE

Crispy Pork and Seafood with No Fork

This guide is part of our Good Eats series where we find food spots around the city that we think are worthy of going out of your way to visit. We have two places in store for this guide. The first is on the Southside in Bronzeville where you can have a traditional Louisiana-style seafood boil and the second is a massive Filipino grocery store (Seafood City Market) on the Northwest side in Albany Park. Here are the highlights.

01 Two Fish Crab Shack
02 Seafood City Market
BRIDGEPORT

Art Meets Friday

It's the third Friday of the month and that means hundreds of artists in Bridgeport open up their studios to the public. Tonight we're headed to a few different venues that feature a wide range of multi-disciplinary artists with many hosting interactive demonstrations and special events inside their space. Here are the highlights.

01 Bridgeport Art Center
02 Chicago Maritime Museum
03 Zhou B Art Center
WEST TOWN

Shenanigans

Follow along with our shenanigans and embark on this 3-stop cocktail tour in West Town that ends with deliciously juicy burgers and whatever self-respect you may have left. Here are the details:

01 The California Clipper
02 Sportman's Club
03 EZ Inn
04 Fatso's Last Stand
ELSTON INDUSTRIAL CORRIDOR

A Date Behind an Abandoned Warehouse

Hidden amongst factories and warehouses in Chicago’s Elston Industrial Corridor, we will eat, drink, and jam to live music. Here are the highlights.

01 Ada Street
02 The Hideout
ARLINGTON HEIGHTS, IL

Ramen at the Largest Japanese Market in the Midwest

This guide targets a very specific demographic of people who love Japanese food and culture and are willing to travel to the Northwest Chicago suburbs. We're here to visit the largest Japanese market in the Midwest.  Here are the highlights.

01 Mitsuwa
02 Books Kinokuniya
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