We all know the standard Chicago drill.
You take your out-of-town friends to The Bean, you grab a slice of deep dish that takes 45 minutes to bake, and maybe you brave the crowds at Navy Pier if you’re feeling patient.
We love those spots, but let’s be honest—they don’t really capture the wonderfully strange personality of this city.
Chicago has a gritty, eccentric, and sometimes downright bizarre underbelly that locals know and love. We are a city of history, sure, but we’re also a city of ghost stories, underground tunnels, and very specific oddities.
If you are looking to shake up your weekend routine or show a visitor something they definitely won’t find in the standard guidebook, we have you covered.
We dug deep to find the spots that make you scratch your head and say, “Wait, that’s here?”
Here is your guide to the most unique and unusual things to do in Chicago right now.
1. Shit Fountain
Yes, that is the actual name. No, we are not making this up. While the rest of the city is taking selfies in front of shiny metallic beans or lions wearing helmets, residents of Bucktown know about a much quirkier landmark located at 1001 North Wolcott Avenue.
This bronze sculpture is exactly what it sounds like: a beautifully crafted coil of poop. It sits right in front of a private residence. The backstory is pure Chicago petty revenge.
The artist, Jerzy S. Kenar, reportedly got so sick of neighbors letting their dogs foul up his flowers that he created a permanent tribute to the mess. It is technically a fountain, with water trickling down the bronze coil. It is weird, it is hilarious, and it makes for the most confusing photo op you will ever post on Instagram. Just remember, it’s a residential street, so take your photo and keep it moving.
📍 How to get there: 1001 N Wolcott Ave, Chicago, IL 60622 (Bucktown)
2. Turtle Racing at Big Joe’s
Forget the Bears or the Bulls for a minute. The most electric sporting atmosphere in the city happens on Friday nights at a nondescript dive bar in North Center. Big Joe’s has been running live turtle races for decades, and the energy is absolutely unhinged.
Here is how it works: You buy a drink (cheap domestic beer is the move here), and you get a raffle ticket. If your number is called, you get to be a “jockey” for one of the turtles.
The turtles are placed in the center of a ring on a pool table, the glass is lifted, and the first one to the edge wins. The crowd screams like it is the seventh game of the World Series. It is chaotic, cash-only, and easily one of the most fun nights out you can have in the city.
📍 How to get there: 1818 W Addison St, Chicago, IL 60613 (North Center)
👉 https://bigjoesturtleraces.com/
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3. The Chicago Magic Lounge
If you walk past 5050 North Clark Street in Edgewater, you might think you are looking at a laundromat. There are washing machines, a checkerboard floor, and nothing else. But this is Chicago, so things are rarely what they seem.
Walk up to the washing machines and you will find the secret door. Once you push through, you are transported out of a laundromat and into a stunning, multi-level Art Deco speakeasy.
The Chicago Magic Lounge is dedicated to “Chicago Style” magic, which is historically performed close-up at a table rather than just on a big stage.
You can order a craft cocktail and have a magician fool you from two feet away. It feels like stepping back into the 1930s.
📍 How to get there: 5050 N Clark St, Chicago, IL 60640 (Edgewater)
👉 Website: https://www.chicagomagiclounge.com/
4. Woolly Mammoth Antiques and Oddities
Some antique stores smell like lavender and sell nice porcelain teacups. Woolly Mammoth in Andersonville is not that kind of store. This place is a cross between a museum, a science lab, and a fever dream.
The shelves are packed with taxidermy (everything from squirrels to badgers), vintage medical tools that look terrifying, old maps, and even human teeth. It sounds morbid, but the vibe is actually incredibly cool and educational.
It feels like digging through a Victorian cabinet of curiosities. You might not buy anything—though they have great t-shirts—but simply walking through the aisles is an experience in itself.
📍 How to get there: 1513 W Foster Ave, Chicago, IL 60640 (Andersonville)
👉 Website: https://www.woollymammothchicago.com/
5. The Thorne Miniature Rooms
Most people go to the Art Institute of Chicago for the Impressionist paintings or the modern wing. But if you head downstairs, you will find something that is weirdly mesmerizing.
The Thorne Miniature Rooms are a collection of 68 tiny, obsessively detailed dioramas of European and American interiors.
These aren’t just dollhouses. They were constructed in the 1930s on a scale of one inch to one foot, and the craftsmanship is insane. The rugs were hand-woven. The tiny books have paper pages. The light fixtures actually work. You can stare at a single room for twenty minutes and keep finding new details. It is quiet, dark, and transports you to a different world instantly.
📍 How to get there: 111 S Michigan Ave, Chicago, IL 60603 (The Loop – Inside the Art Institute)
👉 Website: https://www.artic.edu/highlights/12/thorne-miniature-rooms
6. Graceland Cemetery
Did you know that the architects and titans of industry who literally built Chicago—from Daniel Burnham to Marshall Field—are resting together at Graceland Cemetery? It is widely recognized as one of the most historically significant burial grounds in the country.
At first glance, with its lush canopy, lake, and winding roads, it looks more like a certified arboretum than a graveyard. But as you walk the paths, you will run into stunning architectural masterpieces and local legends, including the haunting, hooded “Eternal Silence” statue and the massive mausoleum of Potter Palmer.
It is an open-air museum of art and history hidden behind high brick walls. It’s peaceful, hauntingly beautiful, and a perfect spot for a quiet, reflective stroll.
📍 How to get there: 4001 N Clark St, Chicago, IL 60613 (Uptown)
👉 Website: https://www.gracelandcemetery.org
7. The Leather Archives & Museum
Chicago has a deep, significant history when it comes to the leather, fetish, and kink communities, and this museum in Rogers Park preserves that heritage. It is one of the only institutions of its kind in the entire world.
The exhibits cover the history of the leather lifestyle, BDSM culture, and the clubs that defined the scene in decades past. It is an adult environment (18+ only), but it is handled with immense respect and educational intent.
It offers a look into a subculture that has had a massive influence on the city’s identity, even if it’s rarely talked about in mainstream guidebooks.
📍 How to get there: 6418 N Greenview Ave, Chicago, IL 60626 (Rogers Park)
👉 Website: https://leatherarchives.org/
8. The Pedway System
If you work in the Loop, you know. If you don’t, this might blow your mind. There is a whole other city beneath the downtown streets.
The Pedway is a network of underground tunnels and overhead bridges that connects over 50 buildings, train stations, and hotels.
You can walk from City Hall to the Cultural Center to the train without ever stepping foot outside. It is a lifesaver in February when the wind chill is -20, but it’s also a strange place to explore.
You’ll find underground stained glass exhibits, random cafes, shoe repair shops, and hallways that look like they haven’t changed since 1980. Navigating it without a map is a rite of passage.
📍 How to get there: Multiple entrances, including Block 37 and the Chicago Cultural Center.
👉 Website: https://www.chicago.gov/city/en/depts/cdot/provdrs/ped/svcs/pedway.html
9. Oz Park
Did you know the author of “The Wizard of Oz,” L. Frank Baum, lived in Chicago while writing the book? We embrace that claim to fame at Oz Park in Lincoln Park.
At first glance, it looks like a normal neighborhood park with tennis courts and a playground. But as you walk the paths, you will run into life-sized bronze statues of the Tin Man, the Scarecrow, the Cowardly Lion, and Dorothy herself.
It is a surreal little slice of storybook magic right in the middle of the city. It’s charming, a little weird, and a perfect spot for a walk with a coffee in hand.
📍 How to get there: 2021 N Burling St, Chicago, IL 60614 (Lincoln Park)
👉 Website: https://www.chicagoparkdistrict.com/parks-facilities/oz-park
10. Museum of Surgical Science
We have world-class museums here, but this one is in a league of its own. Located in a breathtaking historic mansion on Lake Shore Drive in the Gold Coast, this museum is dedicated entirely to the history of surgery.
The contrast here is wild. You are standing in a room with marble fireplaces and high ceilings, looking at an iron lung or an amputation kit from the Civil War. They have thousands of artifacts, including skeletons, ancient tools, and X-ray machines. It is fascinating, slightly spooky, and gives you a serious appreciation for modern medicine. It is a great spot to hit if you want culture but want to skip the crowds at the Field Museum.
📍 How to get there: 1524 N Lake Shore Dr, Chicago, IL 60610 (Gold Coast)
👉 More information: https://imss.org/
