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Ultimate Offbeat Guide to Chicago, Illinois

Dog poop statues, burgers named after metal bands, and the world's oldest occult store. Chicago is home to some of the best offbeat travel in the country!

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Created by chelsealove32 - April 23rd 2016

The Windy City is one of the most traveled to spots in the country, and for good reason. If you're headed to Chi-Town, why not add a dash of weird to your trip and add some of these offbeat travel ideas to your itinerary!

1524 N Lake Shore Dr, Chicago, IL, US

International Museum of Surgical Sciences

This small museum on Lake Shore Drive is the perfect size, specific enough to be fascinating, but not too large and overwhelming that museum-fatigue sets in. The International Museum of Surgical Sciences is a strange but effective mix of scientific and surgical ephemera, and art based on the body. There are iron lungs, old-school surgical equipment, technical analysis of viruses and infectious diseases, plasticized circulatory systems (a la ‘Body World’) and enormous cringe inducing gallstones. The museum also features a hall of larger-than-life sculptures which commemorate pioneers in medicine and surgery from ancient Egyptian times to the present. Additionally, the museum hosts contemporary artists-in-residence who create works about science and the body, inspired by the holdings of the museum.

WARNING: This is not a museum for the squeamish, 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.

55 North Michigan Avenue, Chicago, IL, US

Cloud Gate

It's true, the Cloud Gate really does looks like a giant silver lima bean... in an awesome way, of course! You cannot visit Chicago without taking your picture in front of it. Standing 33 feet tall, the famous art installation was inspired by liquid mercury, which distorts the city's skyline. 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!

Photo of 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, which has been 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".

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

Chicago Skydeck

Most people point to the Skydeck, glass-floored boxes that jut out 4 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.

Photo of Oz Park
4.4

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

Oz Park

Oz Park is one of Chicago's hidden gems, this park is 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.

Photo of Prayer Booths at the Navy Pier
3.2

600 E Grand Ave., Chicago, IL, US

Prayer Booths at the Navy Pier

If you need to take a 5 and say a few Hail Mary's, don't worry because the Prayer booths at the Navy Pier have got you covered. Installed in order to bring Chicago's a little closer to God, the Prayer Booths are free to anyone looking to make a quick collect call to the big guy upstairs.

Photo of The Peninsula Chicago
4.5

108 E Superior St At North Michigan Avenue, 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- you only have 3 glorious hours to cram as much food as you can into your mouth at the at the all-you-can-eat chocolate buffet. It’s pricey, 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!

756 N Milwaukee Ave, Chicago, IL, US

Intuit: The Center for Intuitive and Outsider Art

This center and museum is the only non-profit in the US that is 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 artist 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.

1852 W 19th St, Chicago, IL, US

National Museum of Mexican Art

Hardly unknown, this museum is nonetheless far enough off the tourist track to be missed by most out-of-town visitors. This small, beautiful museum houses an awesome collection of contemporary works by Mexican artists and artifacts and crafts from Mexican culture, including an impressive array of Day of the Dead memorabilia. The bonus of visiting this museum is getting to have a fantastic lunch afterwards at one of the restaurants in this vibrantly Mexican neighborhood. Keep and eye out for the murals of our lady of Guadalupe, listen out for the Spanish spoken by the residents, and watch your feet as you step over Mayan-seal man-hole covers.

Photo of 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. 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.

Photo of Occult Bookstore
4.3

1164 N Milwaukee Ave, Chicago, IL, US

Occult Bookstore

The Occult Bookstore on Milwaukee Street is the oldest metaphysical store in the country, and specializes in rare artifacts, books, relics, tools, occult art, and more 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 lecture about the spirit world, either way you'll learn something wonderfully weird.

Photo of The Boring Store
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1331 N Milwaukee Ave, Chicago, IL, US

The Boring Store

If you are totally not a secret agent, then shop here! This cute spy-themed store 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? Sweet!

2622 N Clark St, Chicago, IL, US

The Wieners Circle

Not only is The Wieners Circle famous for its amazing Chicago-style hotdogs, cheese fries, and burgers, it's also the place where you can expect a little verbal abuse from the employees, but it's all in good fun. The established 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.

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3514 N Sheffield Ave, Chicago, IL, US

Wrigley Hostel

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If you're not looking to spend a ton of cash on hotel bills, you don't have too! Wrigley Hostel is one of the city's coolest hostels, partly because it offers guests free pub crawls, movie nights, trivia nights, and really makes an effort to create a 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, and even has a 24-hour hang out room with pool, darts, games, and a general camp vibe.

2900 W Belmont Ave, Chicago, IL, US

Kuma's Corner

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. The burger joint, which has a stellar reputation for being one of the coolest (and most delicious) restaurants 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 Zepplin burger, which you have to hold together with waffle fries. Make sure to bring plenty of cash, because the staff aren't fans of using cards.

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 Chicagoans with their collection of naughty bits and bobs for years.

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 the 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.

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 best. Filled with vintage taxidermy, real human skulls, and the most bizarre taxidermy 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 taxidermied giraffe? Yep, they've got that too.

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