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Ultimate Offbeat Guide to Chicago, Illinois

Poop statues, turtle races, & occult bookstores are just the beginning!

  • 18
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Created by Roadtrippers - March 30th 2016

The Windy City is one of the most traveled-to cities in the country (and for good reason!) but few get to experience the stranger side of Chicago. If you're headed to Chi-Town, why not add a dash of weird to your trip? From quirky tours to niche museums to fascinating art, here are some of the coolest ways to get weird in the Windy City!

International Museum of Surgical Sciences
4.0

1524 N Lake Shore Dr, Chicago, IL, US

International Museum of Surgical Sciences

The International Museum of Surgical Sciences is a strange but effective mix of scientific and surgical ephemera. You'll see iron lungs, old-school surgical equipment, technical analyses of viruses and infectious diseases, plasticized circulatory systems (a la ‘Body World’) and enormous cringe-inducing gallstones.

WARNING: This is not a museum for the squeamish, so unless you think you can stomach seeing a plasticized body cut into one inch slices and spread the length of a room, you should steer clear.

Tips: Entry costs $15, and you can plan on spending at least an hour and a half if you're rushing through. Student? Bring your ID and save five bucks.

55 North Michigan Avenue, Chicago, IL, US

Cloud Gate

Standing thirty-three feet tall, Chicago's famous Cloud Gate art installation, which distorts the city's skyline, was inspired by liquid mercury, and looks pretty insane up-close.

It's true that you're probably going to have to fight your way through the crowds of tourists who are always there, but regardless, you still have to do it, because it's a Chicago staple!

Tip: "The Bean" is best experienced on a sunny day with lots of clouds, which results in a strange flowing river effect.

Not Your Mama's Bus Tour
4.0

1331 S. Michigan, Chicago, IL, US

Not Your Mama's Bus Tour

Not Your Mama's Bus Tour is a non-profit tour company that is in the business of helping members of the Chicago homeless community turn their lives around. Passengers are taken on a tour of the city, all while being serenaded with music and powerful short stories, all written by former homeless people.

The tour, which has only been beating the concrete since last year, takes guests to some of Chicago's most famous off the beaten path stops, including filming locations from "E.R" and "Chicago Hope", Chicago's Civic Center, and even the former site of the series "Good Times".

Chicago Skydeck
4.5

233 S Wacker Dr, 103rd Floor, Chicago, IL, US

Chicago Skydeck

Most people point to the Skydeck, glass-floored boxes that jut out four feet from the 103rd floor of the Willis Tower, as the prime source of pants-pooping fear in Chicago, but if you're brave enough to venture out, you'll get some awesome selfies.

Tips: Expect to pay about $22, and if you get there before 10:30am, you can pretty much beat the crowds. The elevator to the Skydeck is an attraction in and of itself - you'll climb over 100 floors in less than a minute!

Oz Park
3.8

2021 N. Burling St., Chicago, IL, US

Oz Park

Oz Park is one of Chicago's hidden gems. It's completely Wizard of Oz-themed, with statues of all the major characters. Sorry Wicked Witch fans, the famous green villain is the only character missing her own statue. And yes, Dorothy is sporting her ruby slippers!


Prayer Booths at the Navy Pier
4.0

600 E Grand Ave., Chicago, IL, US

Prayer Booths at the Navy Pier

If you need to take a five and say a few Hail Marys, don't worry, because the prayer booths at Navy Pier have got you covered. Installed in order to bring Chicago a little closer to God, the Prayer Booths are free to anyone looking to make a quick collect call to the Big Guy Upstairs.

The Peninsula Chicago
4.5

108 E Superior St, Chicago, IL, US

The Peninsula Chicago

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Looking for something to do on a Friday or Saturday night? Head to the Lobby of The Peninsula at 8pm on the dot, because you only have three glorious hours to cram as much chocolate as you can into your mouth at the at this hotel's all-you-can-eat chocolate buffet. It’s pricey at $30 a head, but it’s worth it.

The Peninsula is one of the most lavish hotels in the city, and the chocolate is of the highest quality. We’re talking high-end confections like truffles, chocolate-dipped strawberries and chocolate pot de crème, plus beverages like lavender-scented white chocolate cocoa. There’s usually between 10-15 options, so start fasting now!

Tip: Pay an extra $10 and you'll get their exclusive chocolate martini with the buffet!

Intuit: The Center for Intuitive and Outsider Art
5.0

756 N. Milwaukee Avenue, Chicago, IL, US

Intuit: The Center for Intuitive and Outsider Art

The Center for Intuitive and Outsider Art is the only non-profit in the country that's focused entirely on the work of self-taught and outsider artists. The exhibitions display a rotating assortment of more then 1,100 works of art.

One of the more well-known outsider artists, Henry Darger, lived in a one room apartment in Chicago for most of his life, writing and illustrating a15,000 page saga detailing the adventures of the mythical ‘Vivian Girls’, which was discovered after his death. The Intuit Center came into possession of much of his work and furnishings, and has re-created his room in the museum, giving you a glimpse into Darger’s extraordinary and strange mind.

Tips: The museum isn't huge, but entry is only $5, making it well worth the visit. Expect to spent about 45 minutes exploring the exhibits.

National Museum of Mexican Art
4.3

1852 W 19th St, Chicago, IL, US

National Museum of Mexican Art

The National Museum of Mexican Art is a small, beautiful museum that houses a unique collection of contemporary works, artifacts, and crafts, including an impressive and stunning array of Day of the Dead memorabilia.

Tip: The bonus of visiting this museum is getting to have a fantastic lunch afterwards at one of the restaurants in this vibrantly Hispanic neighborhood.

Shit Fountain
4.1

1005 N. Wolcott Ave, Chicago, IL, US

Shit Fountain

The bronzed “coil” sits proudly atop a marble pillar on Augusta Boulevard, daring all “crappy” dog walkers to leave behind a “dog pile”. Water ripples from the top of the statue as a subtle war cry, telling all 4-legged passers-by to keep on walking.

The gross fountain is on private property, but that hasn’t stopped sightseers from taking a peek and snapping a poo-poo profile pic of their own.

Tip: If you’re interested in checking out the turd memorial, remember to respect the homeowners and stick to the sidewalk… that goes for your pooch too.

Occult Bookstore
4.3

1578 N Milwaukee Ave, Chicago, IL, US

Occult Bookstore

The Occult Bookstore on Milwaukee Ave is the oldest metaphysical store in the country, and specializes in rare artifacts, books, relics, tools, occult art, and other things you won't find at the corner store. They also offer a series of classes that range from spirit communication to a lecture series about some of the rarer books in the store. Pick up a good luck charm or take in a talk about the spirit world; either way you'll learn something wonderfully weird.

Tip: Be sure to check their schedule if you plan on visiting - you might be able to catch one of their workshops. Don't worry if you know nothing about spellcasting - you will when you leave!

The Boring Store
4.0

1331 N Milwaukee Ave, Chicago, IL, US

The Boring Store

This cute spy-themed store, which peddles spy glasses, fake mustache disguises, and "burn after reading" stamps among other things, is actually a front for 826CHI, an organization devoted to supporting students ages 6 to 18 with their creative and expository writing skills, and to help teachers inspire their students to write, via tutoring, classes, field trips and more. Secret agent gadgets to support an awesome charity? A must see!

2622 N Clark St, Chicago, IL, US

The Wieners Circle

Not only is The Wieners Circle famous for amazing Chicago-style hotdogs, cheese fries, and burgers, it's also the restaurant where you can expect a little verbal abuse from the employees... but it's all in good fun. The restaurant is open until 5AM (which you've probably already guessed) makes it the perfect place for all the booze-fueled customers coming out of the bars, hungry and ready to offend.

Tip: The meek might want to sit this one out, especially after-hours. It gets loud, shouty, and pretty profane.

Wrigley Hostel
3.9

3514 N Sheffield Ave, Chicago, IL, US

Wrigley Hostel

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Wrigley Hostel is one of the city's coolest hostels, partly because it offers guests free pub crawls, movie nights, and trivia to create a very cool community vibe for everyone who books a bed. The Hostel is located in one of the best neighborhoods, with loads of stuff to do around every corner. They even have a 24-hour hang out room with pool, darts, and videogames.

Tips: Email ahead of your visit: and they'll get you a residential parking sticker which means free parking during your stay. They also offer wash-and-fold laundry service for just $10.

Kuma's Corner
4.5

2900 W. Belmont Ave, Chicago, IL, US

Kuma's Corner

Kuma's Corner, which has a stellar reputation for being one of the coolest (and most delicious) burger joints in the city, has no problem living up to its expectations. Every burger on the menu is named after a famous heavy metal band, including the Led Zeppelin burger, which you have to hold together with waffle fries.

Tips: Kuma's Corner is literally one of the busiest restaurants in the city, so if you're planning on grabbing lunch, be there well in advance. Make sure to bring plenty of cash, because the staff aren't fans of using cards. Seriously. Don't try and use a card. We warned you.

The Leather Archives S&M Museum
3.9

6418 N Greenview Ave, Chicago, IL, US

The Leather Archives S&M Museum

The Leather Archives S&M Museum is organized by, quite possibly, the most meticulous BDSM-loving fetishists on the planet. The leather culture curators have been busy preserving the history of BDSM, leather kink, and fetish lifestyles, and titillating visitors with their collection of naughty bits and bobs for years.

Tip: If you aren't into the leather scene, don't be afraid to ask the museum staff questions. They're super friendly, and won't use any of the crazy contraptions on you... unless you ask them to.

Big Joe's
3.6

1818 W Foster Ave, Chicago, IL, US

Big Joe's

Head down to the racetrack for the most intense gambling experience of your life! This local dive bar features turtle races on weekends, and it gets pretty wild– turtles have never been so exciting, and it’s the only time you’ll ever want your bet to be the slowest animal on the track. The cheap drinks and fun atmosphere make this place a crazy good time, and definitely one of the most unique things to do in Chicago.

Tip: Get there extra early to grab a table, but stick around until the end of the night - most of the crowd turns in early and passes off their spare race tickets to the crowd, which means more chances to win big!

Woolly Mammoth Antiques, Oddities & Resale
4.4

1513 W Foster Ave, Chicago, IL, US

Woolly Mammoth Antiques, Oddities & Resale

Oddity shops are nothing new, but Woolly Mammoth is easily one of the country's weirdest. Filled with vintage taxidermy, real human skulls, and the most bizarre antiques you've ever seen, the shop is a dream-come-true for weirdos looking for the perfect accent to their personal collections. Need a creepy old medical device? They've got that. A pig fetus in a mason jar? Sure! How about a taxidermy giraffe? Yep, they've got that too.

Tip: Ever wanted to learn taxidermy? They offer regular courses!

If you're headed to the Windy City and you're looking to turn your road trip into a wonderfully weird one, look no further. These destinations are guaranteed to satisfy any offbeat adventure itch!

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