Unusual Things to Do in Chicago

Chicago is a city known for its creativity and artistic vibe, so it’s no surprise that various cool, unusual and hidden attractions have sprung up all over the windy city over the decades. Whether you’re looking for weird things in Chicago, unique attractions, or unforgettable experiences, here are some of our favorites for you to explore.

Unique Museums in Chicago

As we’ve mentioned before in our blogs, Chicago is very much the home of arts and science with some of the most internationally famous museums in the world. There are also some unique museums in Chicago that may pique your interest with their quirky charm. The International Museum of Surgical Science aims to inform the public about the history, development, and advances in surgery with some eye-opening exhibitions and displays. You can find over 7,000 medical artifacts spanning centuries of worldwide medical history across the four floors of this fascinating museum. This museum is certainly not for the squeamish and you might find it hard to forget some of the sights.

Meanwhile, if you’re searching for something a bit more lighthearted then the Busy Beaver Button Co. is a lovely goldmine of pin-back button history. With over 9,000 buttons organized by category and date, this museum is a fun and unique Chicago experience. And finally, one for the sports enthusiast, hidden away in Little Italy is a museum dedicated to Italian American sport stars. The National Italian American Sports Hall of Fame boasts hundreds of artifacts including Mario Andretti’s Indy 500 race car, Rocky Marciano’s first heavyweight championship belt, Vince Lombardi’s last coat worn as coach of the Green Bay Packers, and swimmer Matt Biondi’s Olympic gold medals. It’s a lesser-known gem and a great stop for anyone looking for weird things to do in Chicago with a sporty twist.

Strange Shops

If you’re looking for vintage toys or bizarre antiques in a very unique setting, then Wooly Mammoth Chicago is the place for you. Some may find the interior fascinating, others may find it creepy but what can’t be disputed is the eye-catching nature of this shop that features a whole host of bizarro items including antique taxidermy, anatomy items, medical stuffs, books, toys, skulls, and more. Another quirky gem of the city is the Wicker Park Secret Agent Supply Co. On the face of it, this is a place seemingly teeming with every gadget a secret agent spy could need, but delve deeper and you will discover it is the storefront of 826CHI, a non-profit organization that supports and inspires students from 6-18 with their writing skills.

If neither of those options tickle your fancy then perhaps a visit to Dusty Groove will? This shop sells old vinyls and LPs and will delight any “vinyl junkies”. Here you can find some rare blues, jazz, hip-hop, and soul records as well as a variety of other genres. There are very few vinyl record stores quite like this in the world.

Unique Food and Drink Experiences

Do you fancy a completely unique dining experience? Then head on over to El Ideas where you can enjoy an adventurous menu in a vibrant atmosphere where guests are encouraged to interact with the chefs in a restaurant with no divides. Described as a cross between an underground dinner party and a Michelin-star experience, it’s one of the most unique Chicago experiences for adventurous foodies.

Are you looking for restaurant customer service even more leftfield? Then check out Ed Debevic’s, which is an old-style American diner that teases and messes with customers, even heckling them. You can expect some surprising scenes at your table as you eat so make sure you are prepared to laugh rather than cry at the service you receive.

If you want to taste something truly unique then head to CH Distillery and ask for a shot of the 70-proof alcohol of Jeppson’s Malört. The makers of the drinks seemingly pride themselves on the fact you will almost definitely not like it. The reactions to this infamous drink have made “Malört Face” a meme, adding a bit of humor to this decidedly weird thing to do in Chicago. brought over by Swedish immigrants, the drink is made in Florida, but only the good people of Illinois are still known to drink it.

Other Unusual Places of Interest

Chicago is also home to some unusual statues such as The Man with Fish which can be found outside the famous Shedd Aquarium. Another interesting one is in the Graceland Cemetery, which is the Eternal Silence statue that carries with it a grim-reaper look and a controversial history with many legendary and unsubstantiated rumors over the years following its legend. Both are great examples of unusual things to do in Chicago for those who love offbeat attractions.

The last place we wish to recommend is Oz Park, which was named in honor of L. Frank Baum, the author of the Wizard of Oz who lived in Chicago. And don’t worry, no lions, tigers or bears can be found in the park, well apart from the statue of the cowardly lion of course. Statues of the other three main characters can also be found here, although you’ll have to use your imagination if you want to follow a yellow brick road.

Unusual pieces of architecture can be found all around Chicago such as Calder’s Flamingo on North on State Street. This striking piece of work by Alexander Calder is a unique red color known as “Calder’s Red” which contrasts greatly with its backdrop of black and gray buildings. Other interesting and sometimes strange pieces of architecture can be seen on our Architecture Boat Tour of the city, so book your trip now!