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Photograph: Jason LittleHeavy Feather
Photograph: Jason Little

The weirdest things you'll find in Chicago's bars

Chicago has a wealth of historic bars and dive bars teeming with bits of history and things that are downright weird

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Chicago's bar scene is an incredible amalgamation of gritty dive bars that have been around forever, music venues we can't get enough of, a wealth of crafty breweries and cocktail bars that are always pushing the boundaries. One thing that many of those places have in common is the strange artifacts they house (no, we're not talking about the clientele). From a detective agency to hidden red shoes, here are the weirdest things we've found in Chicago's bars.

RECOMMENDED: Our guide to the best bars in Chicago

The weirdest things in Chicago's bars

  • Dive bars
  • Logan Square
  • price 1 of 4

There's a strong likelihood that you might not notice these things if you're at the Owl past midnight and three sheets to the wind, but you'll find a cassette tape vending machine—yes, a cassette tape vending machine—just in case you happen to still have a player (maybe in your car). There's also a waterfall behind the bar, a remnant of its past as a Mexican restaurant.

  • Cocktail bars
  • Logan Square
  • price 2 of 4

This '70's–themed fern bar has a taxidermied bear in an arrangement of green foliage above its fireplace. And somehow, it totally fits right in among the lush, stylish décor.

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  • Music
  • Rock and indie
  • Ukrainian Village
  • price 1 of 4

Chicago's top rock club houses a few strange artifacts—from baby doll heads that regularly make an appearance to a police car door. You can be spot these items (and quiz the bartenders about their origins) while you listen to your favorite up-and-coming musicians.

  • Dive bars
  • Logan Square
  • price 1 of 4

The Burlington doesn't go out of its way to decorate (it doesn't go out of its way to do much of anything, aside from serving beer and good tunes). But the Logan Square dive does have is a skunk tail hanging above the cash register, which is definitely one way to bring a space to life.

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  • Dive bars
  • Bucktown
  • price 1 of 4

With a vibe that's reminicent of your grandparents' basement, you'll find a good amount of knickknacks at Ed and Jean's, but the one that stands out is the train set running above the bar.

  • Dive bars
  • River West/West Town
  • price 1 of 4

This legendary bar has hosted plenty of musical acts over the years, collecting historic mementos along the way. One of our favorites is a painting of Delta blues guitarist David "Honeyboy" Edwards that was given to the bar by Wilco frontman Jeff Tweedy. Elsewhere, you can admire mounted fish on the walls and an old beer can collection.

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  • Dive bars
  • Lower West Side
  • price 1 of 4

This Pilsen mainstay is a great place to knock back PBRs, and feels a bit like a ’70s-era garage sale. On the walls you'll find a collection of Odd Fellows banners, which are derived from a fraternity founded in 18th century England. Guests regularly try to buy them, but the bar's owners haven't taken anyone up on the offer, yet.

  • Cocktail bars
  • Lower West Side
  • price 2 of 4

Tack Room is tucked in the side of Thalia Hall, serving up classic cocktails like mint juleps. It's a piano bar, complete with skulls and candles lining the walls, which puts a slightly macabre spin on the traditional idea of a "tack room."

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  • Lounges
  • Lower West Side
  • price 1 of 4

Simone's is known for being eco-friendly, and most of the bar's trappings are recycled, so just about everything here is weird and interesting. We're especially fond of the back room, called "the lab" because all of the décor was sourced from a demolished high school.

  • Pubs
  • Bridgeport
  • price 2 of 4

While it's no longer in business, the Active Detective Agency used to be headquartered above Maria's, and a guy named Bill Witsman worked there. Witsman started as a carnival baker before becoming friends with infamous cop and mafia hitman Richard Cain. It's rumored that the duo ran guns to anti-Castro Cubans before they landed in Chicago. Maria'sco-owner Ed Marszewski remembers Witsman as a "great woodworker" who would warn him "about being a left-wing progressive" who should "chill down."

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  • Cocktail bars
  • River North
  • price 2 of 4

If you're up for a hunt, you'll find a small signature design element in select Lettuce Entertain You bars and restaurants: a red shoe. It all started at Hub 51, with a red heel in the rafters derived from a story about an enthusiastic party-goer having a really good time. Look for a red flip flop at Three Dots and a Dash, a crimson cowboy boot at Bub City and a bright high-heeled pump at RPM Steak.

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