Top 17 Things to Do in Chicago: The Only Bucket List You Need
In Chicago, there’s always something brewing—whether that’s a cup of coffee or a lively festival down in Wicker Park. That’s why Chicago is a can’t-go-wrong-with choice if you’re looking for an unforgettable time. Sure, some may call it the Second City, but when it comes to fun and exciting experiences, it's a clear number one.
Planning a trip soon? Be inspired by our bucket list of things to do in Chicago. Tick these adventures off, and you’ll be calling yourself a Chicagoan in no time.
Heart-Pounding Hotspots
In the mood for some palm-sweating, adrenaline-pumping fun? Here are the most thrilling things to do in Chicago:
1. Conquer Your Fear of Heights at Skydeck
What if we told you that you could stand outside Chicago’s tallest skyscraper—at 1,353 feet up? Skydeck Chicago in Willis Tower, one of the world’s tallest buildings, offers the ultimate vantage point, with views stretching as far as four states. On the 103rd floor, step out onto a glass balcony for jaw-dropping views of Chicago all the way to Illinois. With the entire ledge (yes, even the floor) made of glass, you’ll feel like you’re walking on air. Just don’t look down.
Not thrilling enough for you? We dare you to try TILT at 360 Chicago.
2. Defy Gravity at iFLY
Look Ma, no hands!
Here’s a fun thing to do in Chicago for thrill-seekers: make your childhood dream of flying come true at iFLY. Experience an indoor skydiving session that mimics the wind-in-your-face thrill of real skydiving, all from the safety of solid ground. And if you find yourself craving an authentic free-fall experience afterward, make Skydive Chicago your next stop.
3. Jet Ski Across Lake Michigan
Covering Chicago on land is a given. But if you want to make your friends feel some serious FOMO, get on the water, too!
Hop on a waverunner from Chicago Water Sport Rentals and speed across the waves at full throttle. Or take it slow to soak in the views of the city skyline, wave to tourists on sightseeing cruises, or make friends with kayakers along the way. It’s sure to be an experience for the books.
Other Thrilling Things to Do in Chicago
Rock climb at Maggie Daley Park.
Challenge friends to a friendly go-kart race at K1 Speed Chicago.
Chill Hangouts
For days when you want to take it nice and easy, add these chill things to do in Chicago to your itinerary:
4. Bond Over Board Games at Snakes & Lattes
Fun board games, good food, and fantastic company? Count us in.
Swing by Snakes & Lattes for a laid-back time. With a collection boasting over 800 games, Snakes & Lattes is a must-visit for tabletop gamers—whether you’re a die-hard Dungeons & Dragons fan or you simply enjoy a casual game night. Challenge friends to friendly competition while munching on classic game-night bites and sipping on cocktails (or lattes, for obvious reasons).
They also host a variety of events, from puzzle races to trivia nights, offering plenty of opportunities to socialize with fellow gamers. It’s definitely worth timing your visit to coincide with one of their events to fully enjoy these fun things to do in Chicago for young adults.
5. Count the Stars at the Adler Planetarium
Explore the marvels of the universe at the Adler Planetarium. Whether you’re hoping to impress a date or on a solo celestial adventure, this is one of the most fun and unforgettable things to do in Chicago. With exhibits that’ll make you go oooh and aaah (their Sky Shows, in particular, are a visual treat), it’s an experience that’s truly—and literally—out of this world.
6. Tour the Garfield Park Conservatory
Looking to escape the city? Get lost in Garfield Park Conservatory—spanning 12 acres, this botanical garden is home to thousands of plant species. Wander through the dome to marvel at vibrant flora and fauna, or visit their outdoor gardens to admire seasonal blooms in the spring and summer months. With everything from permanent installations to ever-changing displays, there’s always something new to see.
Other Chill Things to Do in Chicago:
Soak up some sun at the North Avenue Beach.
Tap into your inner scientist at the Griffin Museum of Science and Industry.
Foodie Favorites
You don’t need us to tell you to indulge in good food. But just in case you need a little nudge, go ahead—dive into Chicago’s culinary scene and treat yourself to something truly unforgettable.
7. Hop on the Barrel Bus
Brewery tours are always a fun thing to do in Chicago, but you know what makes them even more fun? Getting to ride on a Prohibition-era style barrel bus.
The Barrel Run is one of Chicago’s popular craft beer tours, taking you to three local breweries in style. Hop from one brewery to another in a bus shaped like a giant barrel (talk about immersive), and sample the city’s finest brews while leveling up your knowledge of all things beer.
8. Devour a Chicago Deep-Dish Pizza
You can’t visit Chicago without having a slice (or two, or three, or more) of their famous deep-dish pizza. Chunky, cheesy, chewy, Chicago deep-dish pizza is the ultimate comfort food that’ll make every other deep-dish pizza you’ve tried taste meh.
We won’t name one specific restaurant (mostly because there are too many great options, and, honestly, that’s like asking us to choose our favorite kid). But if you’re looking for some top-rated spots—according to Yelp and Reddit—you can’t go wrong with Lou Malnati’s Pizzeria, Giordano’s, and Pequod’s Pizza.
Other Foodie Favorites in Chicago:
Grab a bite at the black-and-white 2d Restaurant—without a doubt, one of the most fun restaurants in Chicago.
Treat yourself to a Michelin-star meal at Kasama, a Filipino-inspired restaurant.
Try Chicago’s famous Italian beef sandwich by Al’s Beef.
Arts and Culture Escapes
You can’t fully experience a city without immersing yourself in its culture. Here are some activities you can’t miss:
9. Tour Chicago’s World-Class Museums
Chicago is home to countless museums, many of which are free or offer discounted days. This is excellent news if you’re seeking cheap things to do in Chicago.
Head to the Art Institute of Chicago to interpret modern art (or at least attempt to), honor famous writers at the American Writers Museum, or soak up the grandeur of the Chicago Cultural Center. With so many options, choosing which ones to go to can be a challenge, but trust us—whichever you pick, it’s sure to be a worthwhile experience.
10. Experience Chicago’s Jazz Culture at Andy’s Jazz Club
New Orleans may be the birthplace of jazz, but Chicago’s jazz scene is just as vibrant. This makes listening to jazz a must-do whenever you’re in the Windy City. Andy’s Jazz Club is a local gem where you can savor delicious food and drinks, all while being surrounded by smooth sax, rich trumpet riffs, and more. After a night at this iconic spot, you might find yourself adding jazz music to your Spotify playlist.
11. Watch a Live Show at the Chicago Theater
Here’s another fun thing to do in Chicago: catch a live performance at the iconic Chicago Theater. Whether you're into theater or stand-up, this historic venue is known for hosting award-winning acts, including classics like Annie and more modern ones like Ru Paul’s Drag Race All Stars LIVE (we gotta love a venue with range!).
But the Chicago Theatre isn’t just about the shows—it’s also an architectural beauty. Even if you’re not catching a show, a visit to admire its design is 100% worth your time.
While you’re there, don’t miss the Drunk Shakespeare Society behind the Chicago Theater. It’s definitely one of the more unconventionally fun things to do in Chicago—where else can you watch theater with drunk actors?
Other Arts & Culture-Centric Things to Do in Chicago:
Learn about African-American history at the DuSable Black History Museum and Education Center.
Celebrate the city’s street art scene through the Offbeat Street Art Tour.
Visit Robie House to admire Frank Lloyd Wright’s iconic architectural masterpiece.
After-Dark Fun
The fun doesn’t end when the sun sets in the Windy City. If you’re up for some lighthearted shenanigans, here are some thrilling things to do in Chicago at night:
12. Explore the City’s Mixology Scene
Need a nightcap? Chicago’s got you. From classic mixes to futuristic drinks that look more like elixirs, the city isn’t holding back when it comes to crafting shut-up-and-take-my-money drinks. Treat yourself to fancy cocktails at swanky venues like The Whale, or sip on timeless drinks at fun bars in Chicago such as Delilah’s.
To add an element of mystery to your evening, you could even go on the hunt for hidden speakeasies. We dare you to find one without Googling your way there!
13. Dance the Night Away at Chicago’s Hottest Nightclubs
Chicago practically invented house music (a type of dance music), so what better way to spend the night than busting some dance moves?
Hit up Smart Bar for electrifying sets by the world’s top DJs (and their hit Queen dance party every Sunday). Or if you’re in the mood for a night of glamorous clubbing, make your way to TAO Chicago. With its Asian-inspired interiors and neon-lit ambiance, it’s one of the poshest places in the city. Plus, it’s a VIP hotspot, so you might find yourself on the dancefloor with celebrities.
Other Things to Do in Chicago at Night:
Blow off some steam at the Kanya Range Room.
Watch stand-up at Zanies or the Laugh Factory.
Dine and drag at Lips Chicago or the Baton Show Lounge.
Iconic Festivals and Events
Chicago boasts a vibrant festival scene that showcases the city’s best in music, culture, food, and the arts. Plan your visit around these events to experience what makes Chicago so special:
14. Rock Out at Riot Fest
This three-day festival is the ultimate gathering of rock fans—skip it, and you’re setting yourself up for some serious FOMO.
Since 2005, this annual music festival has been bringing the best of punk, rock, metal, and everything in between to Chicago. It’s hosted industry giants like the Foo Fighters, The Cure, My Chemical Romance… and pretty much every other big name on your Spotify playlist.
And if you need a break from the music, Riot Fest has plenty more to keep you entertained, from scavenger hunts to arcade games for all ages—yes, the festival is kid-friendly!
15. Say “Prost!” at Oktoberfest Chicago
Immerse yourself in German culture during Oktoberfest, one of the best things to do in Chicago during the fall. Warm up with endless pours of beer, enjoy bratwurst, and join in the lively Bavarian festivities. Don’t forget to don your best lederhosen or dirndls and celebrate German heritage at iconic spots like St. Benedict's and Tuman's Tap. Prost!
Check Out the Old Town Art Fair
The Old Town Art Fair is a must-attend for any creative soul. Voted as America’s #1 Art Fair, this annual event gathers the nation’s most acclaimed artists for an entire weekend.
Stroll down the historic streets of Old Town, where you can admire exhibits, discover art from both local and national talent, and savor some of Chicago’s best eats. While you’re there, take part in the Garden Walk, where you can explore the vibrant neighborhood at your own pace.
Touristy Must-Dos
Whether you’re a visitor or a local eager to rediscover the city’s iconic landmarks, here are some of the hottest attractions you can’t miss:
16. Snap Mirror Pics at The Bean
Can you really say you’ve been to Chicago if you haven’t taken mirror selfies at The Bean (a.k.a Cloud Gate)? This massive art installation in Millennium Park is a must-see landmark, offering a unique backdrop for all your touristy pics. While posing in front of The Bean is practically a rite of passage, don't worry—licking it for good luck is definitely optional.
17. Stroll Along the Chicago Riverwalk
Looking for free or cheap things to do in Chicago? Walk the 1.25-mile-long Chicago Riverwalk. This scenic path connects four different districts—Market, Civic, Arcade, and Confluence—offering plenty to see and do. Relax at a charming café as kayakers paddle by, snap photos of vibrant street art, or marvel at the architecture towering above you. Or, simply follow the path and see where it takes you. You never know what hidden gems you might discover along the way.
Other Touristy Things to Do in Chicago:
Be the ultimate baseball fan at Wrigley Field.
Explore Chicago’s vibrant neighborhoods, such as Chinatown and Northalsted.
Have fun as the locals do at Navy Pier.
Chicago Called—It’s Waiting for You
This list barely scratches the surface of what Chicago has to offer—cliché, we know, but once you’re there, you’ll see just how many hidden gems and must-do activities are waiting for you. Experience the city for yourself and let Chicago’s streets lead you to your best adventures yet.
And remember, if you’re in the mood for a cozy hangout, you’ve got a table at Snakes & Lattes on Milwaukee Avenue. Book a reservation today.