15 Most Unusual Things To Do in Chicago You Just Can't Miss

Last Updated on September 12, 2023 by Nikki Jain

Chicago, the Windy City, is a haven of entertainment and a great place to visit for aficionados of the obscure. With the bustling metropolis that it is today, it's easy to forget just how much art, culture, and history colors its vibrant streets.

There are a surprising number of unique things to do in Chicago, ranging from the enchanting to the downright bizarre. To help you create your list of delightful and unorthodox attractions for your itinerary, here are the 15 most unusual things to do in Chicago.

Unique Things To Do in Chicago

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1: International Museum of Surgical Science

International Museum of Surgical Science

The Museum Of Surgical Science is operated by the International College of Surgeons. It is housed in a building in Lincoln Park that was once a 1917 private home, complete with a gilded staircase and Italian marble floors. The museum is filled with thousands of objects and artifacts on display. You'll see X-ray machines, apothecary items, uniforms, and acupuncture needles lined up alongside portraits of prominent figures in medical history.

Along the way, you'll learn about the cultural and professional parts of medicine and its various fields, covering topics like quack doctors and plastic surgery. The museum also has an extensive library filled with various rare old books, including works by Florence Nightingale. Meanwhile, modern galleries focus on machinery in medicine and artistic depictions of various medical themes. With the long and sordid history of surgery and all its macabre details, it's no surprise that this is one of the most unusual things to do in Chicago.

Accommodation: Where to stay in Chicago

Address: 1524 N Lake Shore Dr, Chicago, IL 60610

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2: Medieval Torture Museum

Medieval Torture Museum

The Medieval Torture Museum is an eight-room delight featuring some of the most gruesome methods of torture in history. Located on State Street, the interactive location is one of the most fascinating and unusual things to do in Chicago. 

The museum uses an evocative setup of displays with silicone dummies and various torture devices to get its message across. Each exhibit is almost akin to a diorama of gore, with the dummies bearing horrified and pained expressions as they're posed in terrible positions upon each device. 

Each showcase has an informational text wall to provide further information, but the museum also has a free audio guide by an appropriately spooky voice. Regardless, you'll gasp and squeal at the displays, from the "bloody eagle" of the Viking era to the Holy Roman Empire's breaking wheel. You can even safely try out some of the devices with the dummies.

Address: 177 North State Street, Chicago, IL 60601

Website: www.medievaltorturemuseum.com

3: Oz Park

Oz Park
Dreamstime/Jim Roberts

You wouldn't think that one of the most unique things to do in Chicago is sitting right in the very famous Lincoln Park. Oz Park was created as part of a project to improve the dilapidated portions of the neighborhood. Author L. Frank Baum, of Wizard of Oz fame, lived here in the 1890s, making this dedication to his work all the more fitting.

Oz Park's original grounds were acquired by Chicago in 1974. Over time, the park grew into a wonderland, depicting the wonders of the iconic fantasy novel as shown in their 1939 musical adaptation. You'll see statues of the characters, such as Scarecrow, Tin Man, Toto, Cowardly Lion, and Dorothy, scattered about the grounds. Kids will be thrilled by Dorothy's Playlot, a charming themed playground, too!

Address: 2021 N Burling St, Chicago, IL 60614

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Looking to visit other amazing places in Illinois? Check out our lists of tourist attractions in Chicago & tourist attractions in Illinois!

4: Woolly Mammoth Antiques & Oddities

Woolly Mammoth Antiques & Oddities

Looking for unusual curiosities to add to your collection? You'll find them all at Woolly Mammoth Antiques & Oddities. Shopping here is certainly among the quirky things to do in Chicago. There are even various classes included for those who wish to learn about preservation and taxidermy.

Opened by a couple in 2010, the shop is a haven of various bizarre oddities, especially of the medical variety. You'll see used hearing aids, lice powder, urns, preserved animal fetuses, skulls and bones, outdated medical equipment, odd taxidermy, and more at this intriguing location.

Who doesn't love an alligator turned, by taxidermy, into a lamp? There are also some other random, interesting items, like a handmade wooden journal by a Boy Scout from the '60s.

Address: 1513 W Foster Ave, Chicago, IL 60640

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5: Shit Fountain

Shit Fountain
Flickr/Brandie Heinel

If you're looking for weird things to do in Chicago, it hardly ever gets weirder than Shit Fountain. The "fountain" was created by Jerzy S. Kenar, an artist who was tired of dogs doing their business all over his flowers. The statue is a metal sculpture designed to look like, well, a piece of shit. It is set upon a fancy sandstone pedestal that looks like it'd be fitting for a Grecian bust.

The poop sculpture is a "fountain" because it very slowly secrets water into a shallow basin in a rather unflattering way. Though it may be crude, Shit Fountain has become quite a loved part of the community. Plus, it's a part of Kenar's privately owned land, so the city's not concerned with its presence.

Address: 1001 North Wolcott Avenue, Chicago, IL 60622

6: The 606 (Bloomingdale Trail)

The 606 (Bloomingdale Trail)
Dreamstime/Antwon Mcmullen

The 606, also known as the Bloomingdale Trail, is the end result of a longstanding effort to create more active open spaces in Chicago. With the works of various communities, non-profit groups, the Chicago Park District, the City, and the Trust for Public Land, The 606 was created following multiple meetings and points of collaboration.

Today, the Bloomingdale Trail and its contents are signature and unique places to visit in Chicago. The public recreational space has trails for hikers, runners, and bikers, mixing history, art, and design into a utopian and relaxing environment for the whole family.

Address: 1805 N Ridgeway Ave, Chicago, IL 60647

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7: Turtle Race At Big Joe's

Turtle Race At Big Joe's

You've heard all about fast and furious races featuring horses, race cars, and even ostriches. But what about those featuring one of the slowest animals in the world? That's why turtle racing at Big Joe's is one of the most unique things to do in Chicago.

Big Joe's is a joint in Lincoln Park that hosts this "rite of passage" of the city. Those who wish to join the race have to show up and buy drinks and food here in order to earn raffle tickets. Winning tickets get to compete in the turtle race and will be assigned to one of six resident turtles, all with their own names and a lot of love from the community. It's a ton of fun!

Address: 1818 W Foster Ave, Chicago, IL 60640

8: Dusty Groove

Dusty Groove
Flickr/Kyle Akerman

Dusty Groove is a big, airy shop filled with LPs and 45s. It was opened in the early 1990s by some DJs who worked at a radio station at the University of Chicago. They loved scouting the city for records to play at parties or on-air, so they decided to resell their finds to other enthusiasts of the items.

The DJs started selling their vinyl via direct-mail orders, but it wasn't long before their business exploded and became renowned across the globe. They now carry some of the rarest vintage records and musical oddities at good quality and high prices. Despite its renown, the specificity of Dusty Groove makes a trip here one of the most unusual things to do in Chicago.

Address: 1120 N. Ashland Chicago, IL 60622

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9: The Crown Fountain

The Crown Fountain
Dreamstime/Sergii Figurnyi

The Crown Fountain may be just one of Millennium Park's many fountains, but it's still one of the most unique places to visit in Chicago. It is set on a reflecting pool that's shallow enough for splashers and waders. The fountain stream itself spews out from two towers of glass bricks filled with LED lights that form the videos of one of a thousand residents of the city.

The towers are each 50 feet in height, and every few minutes, the LEDs rotate images to a different person. So what's so special about this? Well, the fountain is designed to look like the water is being spat out of the mouths of the aforementioned people. The videos of the Chicagoans show them smiling, then puckering their lips as a stream of water rushes out from a pipe 12 feet above the ground.

Address: 201 E Randolph St, Chicago, IL 60601

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10: Chicago Magic Lounge

Chicago Magic Lounge

If you want some more quirky things to do in Chicago, look no further than the Chicago Magic Lounge. It offers some incredible shows of genuine Chicago-style magic. What, exactly, is this type of magic? Dating back to the early 1900s, it involves up-close-and-personal magic performed in bars. These illusory tricks are played on small stages, at the bar itself, and even at the tables.

A mix of speakeasy and theater, the Chicago Magic Lounge is the place to go for fans of a good show and some nice drinks. It is situated inside a 1940s laundry building that has been converted into the ideal venue for prestidigitation and cabaret.

Address: 5050 N Clark St, Chicago, IL 60640

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11: Busy Beaver Button Museum

Busy Beaver Button Museum

There's only one museum in the world specifically meant for pinback buttons. It's no wonder, then, that this museum is one of the most unique things to do in Chicago. The Busy Beaver Button Museum was founded in 1995 by Christen Carter, who discovered a love for them in England, prompting her to begin making these badges for record labels and bands.

The museum's collection dates back to the 1800s and continues to grow its exhibits. You'll see band pins, life event badges, holiday buttons, and various political markers. There are even some limited-edition buttons on display and sold in-house and across America!

Address: 3407 W Armitage Ave, Chicago, IL 60647

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Also Read: The Best Museums in Chicago

12: Leather Archives & Museum

Leather Archives & Museum

Anything a little risque is sure to be on a list of unique things to do in Chicago. That's exactly what the Leather Archives & Museum is! It is a celebration of leather and BDSM culture showcased through a variety of equipment exhibits, artifact displays, and a huge literature library.

You'll learn about all sorts of things at this museum as you view chains, whips, handcuffs, bondage equipment, leather clothing, and a basement dungeon. There's a surprising amount of depth to this not-safe-for-work location, with information on the culture of fetishism, its role in the LGBT community, and academic discussions on the topic of the taboo.

Address: 6418 N Greenview Ave, Chicago, IL 60626

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13: No Pants Subway Ride

No Pants Subway Ride

Have you ever had a dream that you're in a public space and you've forgotten your pants? The No Pants Subway Ride, as one of the weird things to do in Chicago, lets you experience that for real! This annual winter event involves a group of subway passengers removing their pants before boarding a train.

They must behave entirely normally and remain committed to acting as if nothing is amiss, ignoring the confused stares. Though the No Pants Subway Ride is a national event, it's a pretty big deal in Chicago. It usually happens on the Red Line of the CTA, starting at Loyola Station and coming to a close in the Loop.

14: Graceland Cemetery

Graceland Cemetery
Dreamstime/Eddie Rodriquez

Visiting a cemetery isn't a typical holiday activity. That's why a trip to Graceland Cemetery is one of the unique things to do in Chicago. The graveyard opened its doors in 1860 and has since become home to various famous local architects. Each of these design experts has a suitably elaborate and detailed monument as their marker, which makes a stroll through the cemetery quite interesting.

You'll be surprised at the variety of tombs at Graceland Cemetery. You'll find the final locations of Allan Pinkerton, Kate Warne, Daniel Burnham, Louis Sullivan, and more! From the simple to the incredibly opulent, even the graves of the less famous are intriguing to explore.

As long as you're respectful, this is a somber and melancholy glimpse into the past. You can also join tours of the cemetery, as conducted by the Chicago History Museum and Chicago Architecture Foundation.

Address: 4001 N Clark St, Chicago, IL 60613

15: The Wieners Circle

The Wieners Circle
Flickr/Nicolas Henderson

From its punny name alone, it's probably easy to tell that visiting The Wieners Circle is one of the unique things to do in Chicago. What started out as a simple hot dog joint has turned into a business notorious for its hostile treatment of customers.

It was set up in 1983 by Larry Gold, who just wanted to operate a standard business for hungry bar-goers. But after being annoyed by a wealthy patron ignoring him, shouted "Hey asshole" to get his attention.

From then on, the shouting and name-calling got progressively worse. With a staff predominantly composed of people of color, the yelling at the affluent, mostly white clients has only escalated since Gold's first fateful insult. The business has doubled, and people seem to love the reputation that The Wieners Circle has gained. If you want good hot dogs sold by a family and loyal staff - and you don't mind a little hostility - grab some char-dogs, fries, and chocolate shakes here.

Address: 2622 N Clark St, Chicago, IL 60614

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Wrapping Up

There are lots of unusual things to do in Chicago, each one as vibrant and intriguing as the last. Whether you like the amusing, the gruesome, the spooky, or the artistic, your taste for the strange is sure to be sated in this beautiful and lively city!

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