Fun Things to Do in Chicago That Aren’t Touristy

Looking for unique things to do in Chicago? The Windy City has plenty of off-the-beaten-track attractions to keep you entertained and quite a few hidden gems we particularly love. Here are a handful of things to do in Chicago that don’t involve walking Magnificent Mile or snapping pictures in front of the Bean.

Alternative Shopping 

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Chicago’s most famous shopping street is Michigan Avenue, but if you want to steer clear of overpriced stores and discover some unique treasures head to the streets of these Chicago neighborhoods:

• Lincoln Park – boutiques, one-of-a-kind art, custom leather bags and accessories
• Lakeview – an eclectic mix of local shops, retro finds, designer clothes, original fine art
• Wicker Park/Bucktown – hip vintage shops, vintage couture, trend-making boutiques
• Andersonville – unique only-in-Chicago items, clothing by local artisans, vintage shops. 

Instagram Some Street Art

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Chicago is well known for its vibrant local art scene and there’s nothing better than strolling through a neighborhood and checking out its beautiful murals. You can find some interesting artwork in Wicker Park, Lincoln Park, Pilsen, and South Loop. Not sure what to look for when you get there? Check out this article which outlines a self-guided tour through the three neighborhoods.

Take Yourself on a Chicago Burger Tour

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The humble hot dog with its signature combination of toppings is an iconic symbol of Chicago, but the burger scene in this city definitely needs a shout out, too. From dive bar burgers to high-end gourmet ones, you’ll be blown away by some of the flavor combinations chefs have come up with. Here are some suggestions for tasty burger joints:

• Au Cheval
• Small Cheval
• The Loyalist
• Mini Mott 
• Kuma’s Corner
• Billy Goat Tavern
• The Gage

Tour Historic Theaters

There are lots of historic theaters around Chicago where you can catch a show and take a step back in time. Here are a few to get you started:

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• Biograph Theater – a popular movie house for Chicagoans through the Depression, the place where famous legendary bank robber John Dillinger was shot and killed
• Athenaeum Theater – the oldest continuously-operating off-Loop theater in Chicago, hosts everything from theatrical performances to stand-up comedy
• Chopin Theater – a restored immigrant theater with an emphasis on Eastern and Central European works to stay true to Chicago’s Polish roots 
• The Second City – has seven separate theaters where you can see improv and sketch shows every night of the week; it’s produced comedians like Amy Poehler and Tina Fey
• Theater on the Lake – originally designed as a sanitarium for children with TB, a $7 million event space restoration made it possible for you to catch concerts, theatre productions, and other events

If you fancy a cheap movie, try the MusicBox Theatre in Lincoln Park or Logan Theatre in Logan Square, two local favorites. 

Cozy Pubs & Classy Bars in Logan Square

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Logan Square has some of Chicago’s best drinking establishments and you could easily spend a night bar-hopping around the neighborhood. If you’re looking for excellent ambiance and an immersive drinking experience then try these spots:

• BixiBeer – trendy brewpub with a rooftop patio (check out these other rooftop bars, too)
• Estereo – groove to Latin tunes while sipping Caribbean spirits
• Lost Lake – sophisticated cocktails and Polynesian-inspired dishes
• Young American Bar – cool kid hangout with CBD-infused cocktails; it’s also one of our favorite new restaurants, too
• Heavy Feather – yesteryear drinking den serving craft cocktails
• *Bonus*: Broken English Taco Pub – make a pit stop on your street mural tour and head into the Lincoln Park outpost of this one-stop-shop for mezcal, tacos, and margaritas

Cool Cycling Trails

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Last, but certainly not least, go on an eco-friendly bike ride on the Bloomingdale trail, a three-mile elevated rail-trail that’s part of the 606 system. This urban oasis takes you through some of Chicago’s coolest neighborhoods. You can rent a bike from bike share stations around the city for less than $10 per day or use your own.

You’re a local, why not try a few of these non-touristy things to do in Chicago? Use Zumper to find an apartment that’s near a few of these and you won’t have trouble getting out of the house for some fun.