Yes, we put our pizza sauce on top of the cheese. We spent 108 years blaming a goat for the Cubs' World Series woes. Our "Windy City" nickname has nothing to do with the weather. These aren't the weirdest things about Chicago though. Oh no, it gets much more bizarre.
If you want to explore the strangest corners of this city—we're talking fountains that look like crap, reptile races and taxidermied chipmunks—check these places out.
Updated September, 2025
1524 N. Lake Shore Dr. - Gold Coast
The International Museum of Surgical Science—only for the strong of stomach—explores centuries of international advances in medicinal and surgical practices. If nothing else, you'll leave thankful to be born in the decade that you were.
Have A Few Drinks At Rainbo Club Before Taking A Selfie In Front Of Shit Fountain
1150 N. Damen Ave. - Ukrainian Village
You'll find one of Chicago's most unique public art pieces just a drunk stumble south of world-class dive bar Rainbo Room. Shit Fountain—created by and displayed outside the home of local artist Jerzy S. Kenar—is meant to remind people to pick up after their pooches. It makes for fun Instagram stories, too, though.
Photo: Kater Jayne Photography
1818 W. Foster Ave. - Andersonville
Big Joe's is a quiet, slow-paced, privately-owned neighborhood dive six nights a week. However, on Friday nights, there is a line out the door and down the block. Inside, it's loud and packed. The cause for all the commotion? Some bodacious turtles not named Donatello, Michaelango, Leonardo or—well, you get it. Turtle racing at Big Joe's is a big deal. The more drinks you buy, the more tickets you get. The more tickets you have, the better your chances of landing a "jockey" roll for one of the races. Just don't bet on Jolanda.
Learn a thing or two about the creepy details behind Chicago's storied history via Weird Chicago Tours. Take the Devil & The White City Tour to learn about America's first serial killer—who also made Chicago his home. Get the gritty details of Chicago's past on the Blood, Guns & Valentines Tour. Oh, and there are ghost tours, too. Duh.
1513 W. Foster Ave. - Andersonville
Have an open shelf at home and need the perfect taxidermied rodent to fill it? We've got a suggestion for you. Woolly Mammoth is part-store, part-museum filled with bizarre anatomical, medical, military and downright random objects you can't buy anywhere else.
6418 N. Greenview Ave. - Rogers Park
The Leather Archives is another one of Chicago's lesser-known but most unique museums. Spend an afternoon learning about the fetish/leather subculture including permanent exhibits on women and leather, leatherbars and The Dungeon (we won't spoil this one for you). And, yes, there is a gift shop!
Pimprov at CIC Theater/Image via Facebook
Watch Pimps Do Improv At CiC Theater
1422 W. Irving Park Rd. - Irving Park
Chicago's improv scene is diverse and Chemically Imbalanced Comedy Theater's Pimprov show proves it. As the theater's website states, "It's pimps that improvise. It's that simple." If you're looking for something reverent, respectful and family-friendly, please look elsewhere.
Stroll The Yellow Brick Road At Oz Park
2021 N. Burling St. - Lincoln Park
Okay, we can all agree that The Wizard Of Oz is a cinematic classic, but do we really need an entire park dedicated to it? Superfans will definitely enjoy snapping pictures with sculptures depicting Dorothy, the Scarecrow and other characters. Warning: There is no actual yellow brick road in Oz Park...but you can use your imagination.
3407 W. Armitage Ave. - Logan Square
Passionate about what pinback buttons you choose to adorn your denim jackets with? Get ready for some next level inspiration at the Busy Beaver Button Museum, featuring hundreds of buttons from all eras of the 20th century.
2622 N. Clark St. - Lincoln Park
Weiner's Circle's entertainingly sassy staff is enough to have established its notoriety in Chicago, but there's one menu item in particular that people love to talk about. Here's all we'll tell you: Go up to the window, hand the cashier a $20 bill, ask for a "chocolate shake" and make sure there are no impressionable young children in the immediate vicinity.
5050 N. Clark St. - Andersonville
Chicago's newest theater doesn't host theatrical performances or live music. It's entirely devoted to magic. A secret entrance—no, this isn't you're average Laundromat—gives way to two theater spaces and a cocktail lounge with nightly performers. You can also explore a library full of priceless trinkets from magic's long history and some of its most famous names. Getting out of here without having fun would take an escape artist better than Houdini.
Image Via Facebook/ Medieval Torture Museum
177 N. State Street. - The Loop
Are you brave enough to step foot in Chicago's new Medieval Torture Museum? Labeled as one of the country's most disturbing museums, immerse yourself in a detailed collection of slow death tools and medieval practices that most can't even imagine possible. Do you think you have what it takes to step inside?
Image Via Facebook/ Insect Aslyum
2870 N. Milwaukee Ave - Logan Square
Most people try to get bugs out of their homes, but the new Insect Asylum brings them in! Hundreds of insects from around the world will be displayed at the Asylum's grand opening on May 14th. Unlike other collections, this archive consists of antique insects never seen before. Don't worry; bug spray isn't needed here.
Image Via Facebook / Merz Apothecary
Cure Your Turn-of-the-Century Ailments At Merz Apothecary
4716 N. Lincoln Ave - Lincoln Square
Tucked away on Chicago’s north side is a pharmacy that feels like it time-traveled straight from 1875. Originally opened by Swiss-American pharmacist Peter Merz, this spot once served as an old-world doctor and druggist—and it still smells like it. Think eucalyptus and frankincense wafting through dark oak cabinets stocked with amber-tinted glass jars. Today, it’s part museum, part modern wellness haven, selling everything from homeopathic tinctures to fancy French soaps.
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