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 fashio...

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 gr...

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 ...

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...

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 Linc...

The night starts on an empty street surrounded by warehouses where you'll have cocktails inside a bustling taproom while a forklift might be operat...

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 ...

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...

About an hour outside of Chicago, there are thousands of scientists from all over the world working to answer fundamental questions about space, li...

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 t...

This guide takes us to Chicago's Bridgeport neighborhood, where we'll spend the afternoon doing a reverse progressive lunch. We start with dessert ...

Every neighborhood has that one classic Chicago corner bar that everyone loves. For this guide, we're visiting three neighborhoods and their corner...

When most folks think of Japanese cuisine, they think of either sushi or hibachi. This guide features neither. Instead, we start this guide with Os...

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.'...

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 y...

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 th...

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 ...

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,...

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...

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 ...

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...

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 northernmos...

Oktoberfest celebrations come and go, but this guide lets you enjoy German festive cheer all year round. This guide takes you through Chicago's Nor...

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 Eu...

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...

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 tradit...

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 th...

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...

Andersonville is a literary hub, where bibliophiles and casual book browsers alike will delight in a variety of distinct bookstores. This explorati...

To follow this guide, you’re heading south to the historic and beautiful Bronzeville neighborhood. Combining books, music and history, you’ll expan...

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...

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...

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 ...

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...

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 san...

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’l...

Few things symbolize summer like ice cream and boating, and Chicago offers myriad options to embrace them both. The Chicago River cuts through the ...

Some of the best meals in Chicago can be found in nondescript, no-frills establishments, it turns out. This itinerary will guide you through explor...

As one of Chicago’s most ethnically mixed neighborhoods, West Ridge is a melting pot of cultures and flavors. This diversity is perhaps most preval...

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 leav...

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-frien...

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? T...

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...

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 ...

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 kn...

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 ...

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 a...

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...

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...

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...

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 or...

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 ...

It’s not hard to love Andersonville. It’s a charming North Side pocket of eclecticness and eccentricity just waiting to be tapped. This neighborhoo...

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 pu...

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...

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 rhyt...

Ravenswood, Wrigleyville’s cozy sibling to the north, is home to Chicago’s Malt Row. With Ravenswood Avenue hosting more than 10 craft breweries an...

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 an...

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...

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 vibran...

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 c...

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 t...

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 tav...

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 gu...

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...

About 18,000 years ago, Illinois and Wisconsin were covered under a big sheet of glacial ice.  Eventually, these massive glaciers began to retreat,...

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...

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 ...

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 b...

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 b...

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 h...

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 ...

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 bu...

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 t...

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 f...

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 ...

This guide has you visiting West Ridge, a quiet residential North Side neighborhood that's home to a vibrant South Asian, Jewish, and Eastern Europ...

In this guide, you’ll be taking in the history of Edgewater which encompasses several smaller neighborhoods like Edgewater Beach, Edgewater Glen, M...

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 c...

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. Afterwa...

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...

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 anythi...

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...

No matter the weather, it's worth venturing Chicago's Lakeview neighborhood and making several stops on Southport Avenue, a thoroughfare bustling w...

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 th...

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 disconcer...

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 ...

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, yo...

This itinerary is part of our "Known/Unknown" series, where we pair a Chicago landmark with overlooked places nearby. For fans of literature and ar...

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...

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-ni...

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 ...

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 t...

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 p...

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 Canton...

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 Liber...

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 ...

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 crepe...

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 campfi...

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 book...

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...

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 sto...

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 p...

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....

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 i...

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...

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....

This guide takes you on a mini Swedish adventure in Andersonville that works great as a chill Sunday afternoon outing. This is a historically Swedi...

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 h...

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 to...

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 ...

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...

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...

Walking through Chicago's Gold Coast neighborhood is the like the real life version of scrolling through Zillow and daydreaming about the type of p...

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 circum...

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 t...

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 n...

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 co...

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 ...

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'l...

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 woma...

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...

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...

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 you...

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 ...

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...

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, ...

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 airpl...

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 cre...

For many of us Chicagoans, wintertime means hibernating inside, curled under a heavy blanket, and waiting for the worst of winter to pass.  Well fo...

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 c...

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 d...

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 se...

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 y...

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...

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 g...

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 ...

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-p...

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 physica...

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...

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 w...

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 abo...

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...

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. F...

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 Gr...

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-you...

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. A...

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 starti...

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 evi...

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 guid...

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 ...

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 t...

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...

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'...

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 fiv...

Andersonville is, without a doubt, one of Chicago’s most personality-filled neighborhoods. From its Swedish heritage to its catering towards the LG...

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...

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 h...

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 ...

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 beaut...

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...

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 wit...

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 continue...

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 co...

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 wit...

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...

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 ca...

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 ...

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...

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 ...

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 o...

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 ...

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 ...

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-r...

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

This guide targets a very specific demographic of people who love Japanese food and culture and are willing to travel to the Northwest Chicago subu...