30+ Things to do in Chicago for adults

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Everyone knows Chicago for the Bean, deep-dish, and the skyline. But ask a local, and they'll tell you the best things to do in Chicago for adults happen in neighborhood bars with no sign on the door, in jazz rooms with a century of lore, on the river at dusk, and inside some of the best escape rooms in the Midwest.

Whether you live here or you're in town for a long weekend, this guide covers the fun things to do in Chicago for adults that skip the tour-bus checklist. Consider it your list of unique things to do in Chicago, with a few classics reworked for grown-ups.

Players working the table inside The Heist at The Escape Game Chicago

Unique things to do in Chicago for adults

1. Escape rooms with Morty

The cell block inside Prison Break at The Escape Game Chicago, the top-rated bookable escape room in Chicago on Morty

Escape rooms offer an engaging and challenging activity that sharpens your problem-solving skills, and Chicago has one of the deepest escape room scenes in the Midwest, with more than 150 open rooms within about 25 miles of the Loop. Morty ranks them by thousands of player ratings and lets you compare and book the best of them in a couple of taps.

Start with The Escape Game Chicago, minutes from downtown, where Prison Break is the highest-rated bookable room in the city on Morty and Legend of the Yeti, Special Ops: Mysterious Market, and The Heist round out a polished lineup. Then try Just Escape Room in La Grange for The Haunted Doll Shop and Floor 66, two suburban favorites with top player scores, and PanIQ Room in Fulton Market for The Mob and Voodoo Spirits (there's a second PanIQ in Logan Square with Wizard Trials).

All of them are bookable right inside the app. Gather your friends and test yourselves against themed rooms that range from heists to haunted dolls. It's one of the most fun activities to do in Chicago for anyone who loves a good challenge.

One more worth the drive: 60 to Escape in Schaumburg holds the highest player score in the metro on Morty, led by Lockbuster Video at 81.8 across almost 400 ratings. It doesn't take bookings through Morty yet, so book that one direct.

Check out the top-rated escape rooms in Chicago here.

2. Sip a perfect cocktail at The Violet Hour

The Violet Hour hides behind an unmarked, mural-covered wall in Wicker Park. Inside it's high-backed chairs, candlelight, house rules that keep it civilized, and cocktails made with real care. It's one of the most grown-up adult things to do in Chicago, and a great first stop on a Division Street night.

3. Laugh until it hurts at The Second City

The Second City in Old Town is the improv and sketch school that launched generations of comedians. The mainstage revues are sharp, the drinks flow, and the late sets get loose. It's a Chicago rite of passage and one of the most reliable fun things to do in Chicago for adults.

4. Catch a close-up show at the Chicago Magic Lounge

You enter the Chicago Magic Lounge in Andersonville through a fake laundromat, then settle into an Art Deco cabaret where magicians work table to table before the main show. It's 21 and over, it's clever, and it's one of the most unique things to do in Chicago for a date or a small group.

5. Go tropical at Three Dots and a Dash

Three Dots and a Dash is a tiki bar hidden down an alley in River North, all flaming bowls, rum flights, and skull-shaped glassware. It's a fun, over-the-top escape from the weather and a staple of Chicago nightlife for adults.

6. Play pinball at Logan Arcade

Logan Arcade in Logan Square packs dozens of pinball machines and classic cabinets into a 21-and-over bar with a serious beer list. Bring quarters, bring a rival, and lose an evening. It's one of the best cheap fun activities in Chicago for adults.

7. See a film at the Music Box Theatre

The Music Box Theatre in Lakeview is a 1929 movie palace with a ceiling of drifting clouds and an organist who plays before weekend shows. Indie premieres, classics, and midnight cult screenings all land here. It's a beloved local institution and a perfect low-key date idea in Chicago.

8. Hear jazz at the Green Mill

The Green Mill in Uptown carries more than a century of lore, Capone-era stories included. Live jazz runs most nights (check the calendar) and the Sunday Uptown Poetry Slam is a long-running tradition. It's one of the top things to do in Chicago at night for anyone who wants the real thing, not a tribute act.

9. Catch the blues at Kingston Mines

Kingston Mines in Lincoln Park runs two stages of live blues into the early hours Thursday through Sunday, with bands alternating so the music never stops. It's loud, sweaty, and exactly what the Chicago blues should feel like.

10. Play WhirlyBall in Bucktown

WhirlyBall is lacrosse played from bumper cars, and the Bucktown location adds bowling, laser tag, and a full bar. It's chaotic in the best way and one of the most fun adult activities in Chicago for a birthday or a team night out.

11. Try indoor skydiving at iFLY Chicago

Trying indoor skydiving at iFLY in Rosemont gets you the thrill of freefall without jumping out of a plane. It's one of the most exciting activities in Chicago for adults who crave adventure without too much risk, and it's minutes from O'Hare.

12. Compete in the glowing game rooms at Activate

A team racing across the light-up grid floor at Activate in Oak Brook

Activate is a live-action gaming venue with arenas in Oak Brook and River North: you and your team step into glowing rooms and run, climb, and think your way through timed challenges. It's a workout disguised as a game and one of the more unusual fun things to do in Chicago for adults.

13. Drink where the beer is made at Revolution Brewing

Revolution Brewing's Avondale taproom pours its full lineup, from Anti-Hero IPA to barrel-aged stouts, right next to the tanks. It's a relaxed weekend afternoon and a natural start to a Logan Square and Avondale crawl.

14. Eat your way across town on a Chicago pizza tour

Chicago Pizza Tours takes you by bus to several pizzerias in one afternoon, deep-dish and tavern-style included, with the history served between slices. It's the tastiest way to settle the deep-dish debate and one of the most fun activities in Chicago for adults who plan their trips around food.

Top Things to Do in Chicago for Adults

Cultural & historical attractions in Chicago

15. Get lost in the Art Institute of Chicago

The Art Institute of Chicago holds one of the great collections in the world, from Seurat's Sunday afternoon to the Thorne Miniature Rooms. Go late on a Thursday when the galleries stay open into the evening, and finish at the Modern Wing. It's one of the top things to do in Chicago for adults who appreciate fine art.

16. Tour the Frank Lloyd Wright Home and Studio

The Frank Lloyd Wright Home and Studio in Oak Park is where Wright worked out the Prairie style, and the surrounding streets hold the largest concentration of his buildings anywhere. Pair the house tour with a walk past his neighbors. It's a grounding half day of things to do in Chicago, Illinois for adults curious about why the city looks the way it does.

17. Visit the Museum of Contemporary Art

The MCA in Streeterville is the place for big, bold contemporary shows, and its summer Tuesdays on the Terrace series adds free live music and drinks. It's one of the more relaxed Chicago activities for adults on a weekday evening.

18. Take the Chicago Architecture Center river cruise

The Chicago Architecture Center's river cruise is the classic architecture boat tour: volunteer docents explain the skyline building by building from the water. Pick a late-afternoon departure for the light. It's the classic, done properly, and a highlight of any list of things to do in Chicago for adults.

Outdoor & nature activities in Chicago

19. Walk or ride The 606

The 606 turns an old elevated rail line into a 2.7-mile trail through Wicker Park, Bucktown, Humboldt Park, and Logan Square. Rent a bike, hop off for tacos or a taproom, and hop back on. It's one of the best free things to do in Chicago for adults.

20. Kayak the river at dusk

Urban Kayaks launches from the Riverwalk, so you paddle straight into the canyon of skyscrapers. Sunset tours are the move. It's a new angle on a city you think you know and one of the most unique things to do in Chicago.

21. Escape the cold at Garfield Park Conservatory

The Garfield Park Conservatory is a glass-roofed jungle on the West Side, free for Chicago residents (nonresidents pay admission, and timed entry is recommended) and warm in February. The Fern Room alone is worth the trip. It's one of the best indoor things to do in Chicago for adults when the lake wind turns mean.

22. Watch the sun go down at Promontory Point

Promontory Point in Hyde Park juts into Lake Michigan with a skyline view that beats any rooftop bar. Bring a blanket and a picnic. It's a favorite local date idea in Chicago and costs nothing.

23. Wander the Morton Arboretum

The Morton Arboretum in Lisle is 1,700 acres of trees, trails, and seasonal art installations, and its winter Illumination event (mid-November into early January) lights the woods after dark. It's one of the most peaceful adult activities in Chicago's western suburbs, and a reliably great date.

Entertainment & unique experiences in Chicago

24. See a play at Steppenwolf

Steppenwolf Theatre in Lincoln Park is the ensemble that made Chicago a theater town. New plays, famous alumni, and an intimate house make it the centerpiece of a proper grown-up night out in Chicago.

25. Catch a concert at Thalia Hall

Thalia Hall in Pilsen is an 1892 opera house turned music venue, with a restaurant and a basement cocktail bar in the same building. Dinner, a show, and a nightcap without stepping outside. It's one of the best things to do in Chicago at night.

26. Drink along the Chicago Riverwalk

The Chicago Riverwalk strings wine bars, beer gardens, and City Winery along the water below the Loop. Start at the east end and drift west. It's an easy, polished evening and a smart pick among Chicago activities for adults in warm weather.

27. Drink Glühwein at Christkindlmarket

From late November through Christmas Eve the Christkindlmarket fills Daley Plaza with German wooden stalls, hot spiced wine in collectible mugs, and pretzels bigger than your head. It's the best reason to be downtown on a cold weeknight.

28. See ZooLights at Lincoln Park Zoo

Lincoln Park Zoo is free year-round, and its ticketed ZooLights evenings in winter add more than 3 million lights and, on select nights, an adults-only Adults Night Out with drinks. It's one of the fun things to do in Chicago for adults when the days get short.

29. Watch the Cubs from the bleachers

A summer afternoon at Wrigley Field with the Cubs is about as Chicago as it gets: ivy, a cold beer in the bleachers, and Wrigleyville bars afterward. Even non-fans have a great time.

30. Lean out over the city at 360 CHICAGO

360 CHICAGO on the 94th floor of the former Hancock Center adds TILT, a glass platform that tips you out over Michigan Avenue, plus a bar with the same view. Time it for sunset and one of the top things to do in Chicago for adults becomes a very good drink.

Download Morty for a comprehensive guide to all the fun things to do in Chicago, IL for adults. It's your go-to resource for finding and booking the best escape rooms, haunted houses, immersive experiences, and more. Discover the unique adventures that await you in Chicago with Morty!

FAQs

Does Chicago have a nightlife?

Chicago has a deep nightlife scene, from jazz at the Green Mill and blues at Kingston Mines to cocktails at The Violet Hour, tiki at Three Dots and a Dash, and late sets at The Second City.

What are some things to do in Chicago this weekend?

Good things to do in Chicago this weekend include booking an escape room with Morty, taking the Architecture Center river cruise, biking The 606, catching a show at Thalia Hall, and finishing with a nightcap on the Riverwalk.

What are some unique things to do in Chicago?

Unique things to do in Chicago include entering the Chicago Magic Lounge through a fake laundromat, playing WhirlyBall, kayaking the river at sunset with Urban Kayaks, racing the glowing rooms at Activate, and escaping The Haunted Doll Shop at Just Escape Room.

What are some good date ideas in Chicago?

Great date ideas in Chicago include a film at the Music Box Theatre, sunset at Promontory Point, cocktails at The Violet Hour, winter Illumination at the Morton Arboretum, or teaming up on an escape room.

What are the best things to do in Chicago at night?

The best things to do in Chicago at night include live jazz at the Green Mill, a sunset paddle with Urban Kayaks, sunset drinks at 360 CHICAGO, a late escape room at PanIQ Room in Fulton Market, and the bars along the Riverwalk.

What are some indoor activities Chicago adults can do in winter?

Players leaning over a puzzle inside Board to Death at The Quandary Escape Rooms in Chicago

Indoor activities in Chicago for adults in winter include escape rooms (Legend of the Yeti at The Escape Game fits the season, and Board to Death at The Quandary Escape Rooms is a cozy board-game-themed pick), the Garfield Park Conservatory, pinball at Logan Arcade, the Art Institute, iFLY, and a magic show at the Chicago Magic Lounge.

What are some free things to do in Chicago for adults?

Free things to do in Chicago for adults include The 606, Lincoln Park Zoo, the Garfield Park Conservatory (free for city residents), sunset at Promontory Point, a stroll along the Riverwalk, and browsing the Christkindlmarket in December (the mug of Glühwein is extra).

What is Chicago best known for?

Chicago is best known for its architecture and skyline, deep-dish pizza, the blues and jazz clubs, improv comedy at The Second City, the lakefront, and the Cubs at Wrigley Field. It's also home to one of the largest escape room scenes in the Midwest.

How to spend a day in Chicago as an adult?

Start with coffee and the Art Institute, take the Architecture Center river cruise after lunch, book an escape room in the late afternoon, have dinner in the West Loop, and finish with jazz at the Green Mill.

What are the best things to do in Chicago for young adults?

A team celebrating with their voodoo dolls after Voodoo Spirits at PanIQ Room Fulton Market

Fun things to do in Chicago for young adults include escape rooms at PanIQ Room in Fulton Market, WhirlyBall, pinball at Logan Arcade, a Cubs game and the Wrigleyville bars, live music at Thalia Hall, and Activate in River North or Oak Brook.

Is Chicago fun for adults without kids?

Absolutely. Between the cocktail bars, the jazz and blues clubs, Steppenwolf, the Chicago Magic Lounge, and escape rooms all over the city, Chicago works brilliantly as an adults-only trip.

What are the best escape rooms in Chicago?

The red-lit Doll Shop sign inside The Haunted Doll Shop at Just Escape Room in La Grange

By player ratings on Morty, the best escape rooms in Chicago that you can book right now include Prison Break at The Escape Game Chicago, The Haunted Doll Shop at Just Escape Room in La Grange, The Mob at PanIQ Room in Fulton Market, and Insidious: Return To The Further at Panic Escape Room in Addison. See the full ranked list on the Chicago city page.

30+ Things to do in Chicago for adults (not the usual list!)