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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.

Chicago city skyline with typography of the city's name

Chicago is one of the most traveled-to cities in the country (and for good reason!), and yet, very few get to experience its stranger side. Of course, everyone knows the token sights like the Bean (which actually called the “Cloud Gate”—who knew?), Wrigley Field, and the Skydeck at Willis Tower, but why stop there? If you’ve covered the basics and are looking for a way to go deeper into what the city has to offer, check out these more obscure Chicago sites and attractions!

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International Museum of Surgical Sciences

Science with an Added “Ew” Factor
1524 N. Lake Shore Drive | Gold Coast |

The International Museum of Surgical Sciences is a strange but effective mix of scientific and surgical exhibits. You’ll see iron lungs, old-school surgical equipment, technical analyses of viruses and infectious diseases, plasticized circulatory systems (à la Body Worlds) and enormous cringe-inducing gallstones. Entry costs $15, and you can plan on spending at least an hour and a half—but that’s if you’re rushing through.

Oz Park

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

Source: Shutterstock

There’s No Place Like [Chicago]!
2021 N. Burling Street | Chicago Park District |

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

Indulge in Luxury with the Chocolate Bar at the Pen
108 E. Superior Street | Magnificent Mile |

Looking for something to do on a Friday or Saturday night? Head to the lobby of the Peninsula Hotel at 8 pm 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 per person, but it’s worth it.

Intuit: The Center for Intuitive and Outsider Art

A Museum on a Mission to Celebrate Originality
756 N. Milwaukee Avenue | River West |

The Center for Intuitive and Outsider Art is the only nonprofit museum 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 1,000 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 labyrinth of a mind.

The Violet Hour

An elegant long hallway with wood flooring and large greyish blue curtains with a fireplace at the end of the hall

Source: The Violet Hour

Craft Cocktails Are Hidden Behind This Mural-Covered Entrance
1520 N. Damen Avenue | Wicker Park |

The Violet Hour doesn’t have a neon sign above its door, but thanks to widespread acclaim, it doesn’t need one. This incognito bar on Damen Avenue regularly hires local artists to repaint its outside wall and has some clearly defined etiquette including no baseball caps, no bombs (O, Jager, or otherwise), no light beer, and no reservations. Instead, you’ll get first-rate cocktails, well-dressed patrons, and excellent service.

Sh*t Fountain

This Artist Was Tired of Dogs Doing Their Business in His Garden 
1001 N. Wolcott Avenue | West Town

Jerzy S. Kenar was fed up with owners letting their dogs “go” on his property without picking it up—so the professional artist, who specializes in sculpting, left this friendly reminder to the dog-walkers in the neighborhood. Sh*t Fountain might not be quite as revered as the Bean, but it’s definitely a fun stop to schedule into your visit to Chi-Town.

National Museum of Mexican Art

A group getting a tour of The National Museum of Mexican Art

Source: The National Museum of Mexican Art

Art Sin Fronteras (Without Borders)
1852 W. 19th Street | Pilsen Historic District |

Not necessarily strange but definitely offbeat, 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. With free admission and stunning contents, this celebration of Mexican art leaves you no reason not to visit.

Wicker Park Secret Agent Supply Co.

The exterior front of the Secret Agent Supply Company has a large window with tons of books and novelties to see


Formally Known as the Boring Store
1276 N. Milwaukee Avenue | Wicker Park |

This 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. It also helps teachers inspire their students to write via tutoring, classes, field trips, and more. A feel-good place and a must-see!

Wrigley Hostel

Source: The Wrigley Hostel

Book a Stay at This Super Accommodating Hostel
3514 N. Sheffield Avenue | Wrigleyville |

Wrigley Hostel is one of Chicago’s coolest hostels. Not only is it located in Wrigleyville, one of the best neighborhoods in town (with loads of stuff to do around every corner), but it also offers guests free movie nights and trivia to create a welcoming community vibe for everyone who books a bed.

Kuma’s Corner

Source: Kuma’s Corner

Good Food and Rock ’n Roll
2900 W. Belmont Avenue | Avondale |

With a stellar reputation for being one of the trendiest burger joints in the city, Kuma’s Corner has no problem living up to its expectations. Every burger on the menu is named after a famous rock or heavy metal band—including the Led Zeppelin burger, which you have to hold together with waffle fries. Kuma’s Corner is literally one of the busiest restaurants in the city, so if you’re planning on grabbing lunch, get there well in advance. Make sure to bring plenty of cash because the staff isn’t a fan of credit cards. 

An Alternative Visit to Chi-Town 

Classic tourist spots are always fun, but if you’ve seen them already, why not visit something new? These are some of our favorite offbeat sites to hit in the Windy City—let us know what yours are by tagging us on Twitter

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