The Weirdest Places In Chicago

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. 

Get Squeamish At The Museum Of Surgical Science

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 Innertown Pub Before Taking A Selfie In Front Of Shit Foundation 

1935 W. Thomas St. - Ukrainian Village

You'll find one of Chicago's most unique public art pieces just a drunk stumble south of world-class dive bar Innertown Pub. 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 Snapchats, too, though. 

Photo: Kater Jayne Photography

Turtle Race At Big Joe's

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 (in non-COVID times), 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. 

Play Kinky Trivia At Waterhouse

3407 N. Paulina St. - Lakeview

Themed trivia nights are fun, but when you're done proving how many times you re-watched the same episodes of The Office, come join the real fun at Waterhouse Tavern's Tuesday night Kinky Trivia. It's exactly what you're thinking. Get lucky by proving your sexual knowledge and winning prizes. 

Take A Weird Chicago Tour

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 True Crime And Mystery Tour. Receive eye-opening insight on the city's local sex industry on the Red Light District Sex Tour (no kids allowed). Oh, and there are ghost tours, too. Duh. 

Shop At Woolly Mammoth Antiques & Oddities

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. 

Get Tied Up At The Leather Archives & Museum

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

See Chicago's Biggest Button Collection At The Busy Beaver Button Museum

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. 

Order A Chocolate Shake At Wiener's Circle

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. 

The American Toby Jug Museum/Image via Facebook

Gaze Upon A Record-Setting Collection At The American Toby Jug Museum

900 W. Chicago Ave., Evanston, IL

If you think Toby Jugs are as creepy as we do, this attraction might not be for you. If not, you'll love Evanston's American Toby Jug Museum, featuring more than 8,300 character-based ceramic jugs and free admission! If you have no idea what a Toby Jug is, this is a good place to start

Pick A Card—Any Card—At The Chicago Magic Lounge

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 laudromat—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.