Ultimate Offbeat Guide to Chicago

Chicago is one of the most traveled-to cities in the country (and for good reason!), and yet, very few get to experience its stranger side. Of course, everyone knows the token sights like the Bean (which actually called the “Cloud Gate”—who knew?), Wrigley Field, and the Skydeck at Willis Tower, but why stop there? If you’ve covered the basics and are looking for a way to go deeper into what the city has to offer, check out these more obscure Chicago sites and attractions! 

International Museum of Surgical Sciences

Science with an Added “Ew” Factor

1524 N. Lake Shore Drive | Gold Coast | www.imss.org

The International Museum of Surgical Sciences is a strange but effective mix of scientific and surgical exhibits. You’ll see iron lungs, old-school surgical equipment, technical analyses of viruses and infectious diseases, plasticized circulatory systems (à la Body Worlds) and enormous cringe-inducing gallstones. Entry costs $15, and you can plan on spending at least an hour and a half—but that’s if you’re rushing through. 

“Come on, admit it. You're as fascinated as I am by the strange illnesses, weird maladies, and out of proportion tumors, stones and cysts that can afflict a human body. And just like me, you're also fascinated by the variety of instruments from throughout the centuries and from all over the world, designed to alleviate the suffering and hopefully stave off death. No? Okay, I might be strange that way, but this museum is guaranteed to surprise, educate, or at least disgust you.” -Alice S. on Yelp. 

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Oz Park

There’s No Place Like [Chicago]!

2021 N. Burling Street | Chicago Park District | www.chicagoparkdistrict.com

Oz Park is one of Chicago’s hidden gems. Located in the Lincoln Park neighborhood, It’s completely Wizard of Oz-themed, with statues of the major characters from the book-turned-film. And yes, Dorothy is sporting her ruby slippers!

“Oz Park has quite a bit to offer: plenty of foliage and colorful flowers in the spring and summer, large jungle gyms, basketball courts, and of course, the giant statues of Wizard Of Oz characters. They occasionally do movie nights, and I ALWAYS see a ton of dogs. The park is even gorgeous when it's completely covered in snow during the winter but definitely watch out for gigantic patches of ice.” -Anna K. on Yelp. 

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The Peninsula Chicago

Indulge in Luxury with the Chocolate Bar at the Pen 

108 E. Superior Street | Magnificent Mile | www.peninsula.com

Looking for something to do on a Friday or Saturday night? Head to the lobby of the Peninsula Hotel at 8 pm on the dot—because you only have three glorious hours to cram as much chocolate as you can into your mouth at this hotel’s all-you-can-eat chocolate buffet. It’s pricey at $30 per person, but it’s worth it. 

“Definitely one of the best hotels I've stayed at! . . . While there, we ordered room service several times, had high tea and the chocolate bar at The Lobby, and dinner at Shanghai Terrace . . .  Excited to visit Chicago again in the future because of this hotel!” -Rachael W. on Yelp. 

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Intuit: The Center for Intuitive and Outsider Art

A Museum on a Mission to Celebrate Originality 

756 N. Milwaukee Avenue | River West | www.art.org

The Center for Intuitive and Outsider Art is the only nonprofit museum in the country that’s focused entirely on the work of self-taught and outsider artists. The exhibitions display a rotating assortment of more than 1,000 works of art. One of the more well-known outsider artists, Henry Darger, lived in a one-room apartment in Chicago for most of his life, writing and illustrating a 15,000-page saga detailing the adventures of the mythical “Vivian Girls,” which was discovered after his death. The Intuit Center came into possession of much of his work and furnishings and has re-created his room in the museum, giving you a glimpse into Darger’s extraordinary labyrinth of a mind. 

“Incredible! A glimpse into how unschooled artists express themselves and especially how the life of Henry Darger was captured and preserved so meticulously . . . Anyone who appreciates art should not only visit this wonderful Oasis of the Mundane but become a supporting member as well (it's cheap, folks!).” -Dan H. on Yelp. 

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The Violet Hour 

Craft Cocktails Are Hidden Behind This Mural-Covered Entrance

  1520 N. Damen Avenue | Wicker Park | www.theviolethour.com

The Violet Hour doesn’t have a neon sign above its door, but thanks to widespread acclaim, it doesn’t need one. This incognito bar on Damen Avenue regularly hires local artists to repaint its outside wall and has some clearly defined etiquette including no baseball caps, no bombs (O, Jager, or otherwise), no light beer, and no reservations. Instead, you’ll get first-rate cocktails, well-dressed patrons, and excellent service. 

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‍“I won't ruin it for you, but the inside vibe is amazing. You'll be surprised at how well they pull off the speakeasy scene. The line was long, but we got in within 20 minutes. If you're in Chicago, 100% check out Wicker Park and 100% check out The Violet Hour for the quintessential speakeasy experience!” -Vineeth N. on Yelp. ‍

Sh*t Fountain 

This Artist Was Tired of Dogs Doing Their Business in His Garden 

1001 N. Wolcott Avenue | West Town

Jerzy S. Kenar was fed up with owners letting their dogs “go” on his property without picking it up—so the professional artist, who specializes in sculpting, left this friendly reminder to the dog-walkers in the neighborhood. Sh*t Fountain might not be quite as revered as the Bean, but it’s definitely a fun stop to schedule into your visit to Chi-Town. 

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“I love and celebrate the weird, in just about all its forms. When I travel to new places, I prefer to see that which is off the beaten path . . . In addition to this, you can usually view other works by Kenar, found in and around his studio—all of which are works of beauty and wonder.” -Randy M. on Yelp. 

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National Museum of Mexican Art

Art Sin Fronteras (Without Borders)

1852 W. 19th Street | Pilsen Historic District | www.nationalmuseumofmexicanart.org

Not necessarily strange but definitely offbeat, the National Museum of Mexican Art is a small, beautiful museum that houses a unique collection of contemporary works, artifacts, and crafts, including an impressive and stunning array of Day of the Dead memorabilia. With free admission and stunning contents, this celebration of Mexican art leaves you no reason not to visit. 

“What's not to love about this museum? It's the only Latino museum that's accredited by the American alliance of museums. In addition, it has several interactive exhibitions for kids, families, and adults. Several times a year they host great events that allow them to open their doors at night for adults only. So, if you wanna put your thinking cap on or simply want to have a different experience in the city, pop into here.” -Yayo T. on Yelp. 

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Wicker Park Secret Agent Supply Co.

Formally Known as the Boring Store

1276 N. Milwaukee Avenue | Wicker Park | www.secretagentsupply.com

This spy-themed store—which peddles spy glasses, fake mustache disguises, and “burn after reading” stamps among other things—is actually a front for 826CHI, an organization devoted to supporting students ages 6 to 18 with their creative and expository writing skills. It also helps teachers inspire their students to write via tutoring, classes, field trips, and more. A feel-good place and a must-see! 

“This place is great. It’s a mixture of book store/gag store/random toys and games.  They work with 826CHI, a really cool nonprofit, and this is a great place to grab a gift for children/teenagers, but you can find stuff for people of all ages.” -Anthony L. on Yelp. 

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Wrigley Hostel

Book a Stay at This Super Accommodating Hostel 

3514 N. Sheffield Avenue | Wrigleyville | www.wrigleyhostel.com

Wrigley Hostel is one of Chicago’s coolest hostels. Not only is it located in Wrigleyville, one of the best neighborhoods in town (with loads of stuff to do around every corner), but it also offers guests free movie nights and trivia to create a welcoming community vibe for everyone who books a bed. 

“This is probably one of the nicest hostels I've stayed at! Fresh breakfasts, personal bathrooms, clean/safe feeling place with friendly helpful staff and beautiful little outdoor patio to eat and relax on—great! Super close to transit, and also right by great food, great shopping and good bars. If I'm ever in Chicago again, I'd definitely pick Wrigley to stay at.” -Kyra S. on Yelp. 

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Kuma’s Corner

Good Food and Rock ’n Roll 

2900 W. Belmont Avenue | Avondale | www.kumascorner.com

With a stellar reputation for being one of the trendiest burger joints in the city, Kuma’s Corner has no problem living up to its expectations. Every burger on the menu is named after a famous rock or heavy metal band—including the Led Zeppelin burger, which you have to hold together with waffle fries. Kuma’s Corner is literally one of the busiest restaurants in the city, so if you’re planning on grabbing lunch, get there well in advance. Make sure to bring plenty of cash because the staff isn’t a fan of credit cards. 

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“It's a funny thing, but despite the fact that nearly every spot offers a burger, very few make a great one. Kuma's makes a great one. The Kuma's Original is all you need, cooked perfectly with a delicious egg and bacon on top, seasoned just right . . . Throw in a pretty decent craft beer list, and this is a top spot in Chicago for a great burger.” -Kyle P. on Yelp. 

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An Alternative Visit to Chi-Town 

Classic tourist spots are always fun, but if you’ve seen them already, why not visit something new? These are some of our favorite offbeat sites to hit in the Windy City—let us know what yours are by tagging us on Twitter!