Let's Be Friends

Find Chicago date ideas, Sunday fun day guides, and anything in between

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!
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
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
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
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
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
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.
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
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

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
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
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
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
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
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
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
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)
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
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
Map
Let's Be Friends