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Cool and Unusual

Ultimate Offbeat Guide to Chicago

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.

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

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.

Cloud Gate

Super Moon during a night shot of Chicago's famous Cloud Gate sculpture

Source: Shutterstock

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

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

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 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

Sign at entrance to Dorothy's playground at the Wizard of Oz Park in Chicago, IL

Source: Shutterstock

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!

The Peninsula Chicago

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 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 are usually between 10-15 options, so start fasting now!

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 than 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 a 15,000-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 spend about 45 minutes exploring the exhibits.

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.

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!

Wrigley Hostel

Wrigley Hostel is one of the city’s coolest hostels, partly because it offers guests free 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

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.

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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