Chicago is one of the greatest cities in the world. Am I slightly biased? Sure…but after all my travels, I always love coming back home. After spending over 10 years here, I created this guide featuring unique things to do in Chicago that combines local favorites with typical tourist activities that are actually worth the hype. Make sure to add these experiences to your Chicago itinerary for an unforgettable trip.
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One of the Most Unique Things to Do in Chicago: Visit the Chicago Magic Lounge
One of my favorite unique things to do in Chicago is visiting the Chicago Magic Lounge. Behind what looks like an unassuming laundromat, you will enter a secret passage to find a beautifully designed bar and separate stage area.
Arrive early and stay after the main show to see magic performed at the bar. I highly recommend checking out this venue during their Jazz and Magic night, which is more affordable than their weekend shows.
Laugh the Night Away at iO Theater
Everyone talks up Second City, but I actually prefer io Comedy. Their improv shows are always impressive and I find myself returning time after time. I highly recommend checking out Improv Shakespeare or Whirled News Tonight.
Take a Chicago Architecture Boat Tour
If you’re only going to do one traditional tourist activity in Chicago, make it an architecture boat tour. This is one tourist activity that is definitely worth the hype.
You’ll learn fascinating stories about the buildings that shaped the skyline while enjoying incredible views along the water.
Unique Things to Do in Chicago for Food Lovers: Explore Chinatown and Eat Dumplings
Chicago’s Chinatown is one of the city’s most underrated neighborhoods. Spend an afternoon wandering through the colorful streets, browsing local bakeries, tea shops, and specialty stores. Make sure to visit Qing Xiang Yuan for their famous soup dumplings.
If you don’t feel like exploring on your own, you can always take a Chinatown Food Tour.
Choose Either the Hancock or Willis Tower Observation Deck
I’ve been to both observation decks and I can’t say one view is necessarily better than the other. However, I do prefer the ledge at Sears (Willis) over the tilt at Hancock. Choose either Hancock or Sears Tower (Willis) to visit and if you go around sunset, you’ll have the added bonus of watching the city light up at night after the sun goes down.
Spend an Evening at Chicago's Arcade Bars
Chicago is home to several arcade bars where you can sip a drink while challenging your friends to classic games. My two favorites are Headquarters Beercade and Replay Lincoln Park.
Expect everything from Mortal Kombat to pinball machines from your childhood. They’re perfect for a fun night out, especially if you’re traveling with friends.
Create the Perfect Souvenir at a Spray Paint Studio Class
Most travelers return home with a magnet or keychain. Why not create your own piece of art instead?
A spray paint studio class is one of the most unique experiences in Chicago. Instructors will teach you spray paint techniques and you’ll leave with a one-of-a-kind souvenir that actually means something. Plus this experience is BYOB.
Discover Chicago's Dark Side on a Gangsters and Ghosts Tour
Chicago’s history is filled with mobsters, speakeasies, and ghost stories.
A Gangsters and Ghosts Tour combines all three into an entertaining evening walk through downtown. You’ll hear stories about infamous criminals, haunted buildings, and the city’s darker past while exploring some of Chicago’s most historic neighborhoods.
Catch a Cubs Game at Wrigley Field
Nothing beats spending a summer day at a Cubs game and there are plenty of bars in the area to keep you entertained before and after the game.
I especially love grabbing some pizza at Happy Camper before a game. The recently opened Devious Lounge has thoughtfully crafted cocktails. If you’re looking for a rooftop bar, check out Moe’s Cantina or Old Crow Smokehouse.
Unique Things to Do in Chicago for Adults: See a Burlesque Show at Bordel
For a memorable night out, make your way to Bordel in Wicker Park. This intimate speakeasy hosts burlesque performances in a setting that feels like you’re stepping back in time to the Roaring 20s.
Explore Graceland Cemetery
Graceland Cemetery is the final resting place of many famous Chicagoans. One of the most unique things to do in Chicago is to grab a self-guided tour map from the visitor’s center and wander around to different gravesites while listening to the audio stories on your phone.
Save Money with a Chicago CityPASS
Unique Things to Do in Chicago for History Lovers: Tour the Chicago Theatre
The iconic marquee outside the Chicago Theatre is one of the most photographed spots in the city, but many visitors never step inside.
A guided tour takes you behind the scenes of this stunning venue, where you’ll learn about its history and architecture.
Final Thoughts on Unique Things to Do in Chicago
Whether you’re visiting for the first time or returning for another trip, these unique things to do in Chicago will help you experience both the typical tourist attractions and hidden gems that make the city special.