Oddities, unique experiences, off-the-wall places — if you’re looking for any of the above, Chicago has what you’re looking for. The city’s long-standing history makes space for those who go against the norm for something a little bit off the beaten path.

If you want to embrace Chicago’s wackiness everyday, AptAmigo can help you find luxury apartments with a touch of wacky flair. Learn more our free service, and give us a call.


Experience Wacky Chicago Yourself

1. The Wiener’s Circle

If you would rather have your meal served to you while exchanging barbs laced with profanities, The Wiener’s Circle is a Chicago institution complete with endless stories from both sides of the counter. Patrons coming back from bars on Clark Street in the later hours craving munchies will be greeted with the best of the worst sass around while surrounded with grease on the walls dating back decades, adding to the ambience of the dive. Order the cheese fries and a cheeseburger (or a hot dog with everything on it). By the way, when you order the cheese fries, expect the fries to be marinating in cheese. It’s an experience that saves your life from the 9 a.m. hangover and allows you to enjoy the “day after” and the other restaurants in the neighborhood. The food is served steaming, so it’ll keep you warm during the snowstorms in winter when you’re stumbling home. During the summer… well you don’t care because everyone is outside on the dining benches enjoying the food. The Wiener’s Circle is so popular that even Conan O’Brien & Jimmy Kimmel tried it out.

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2. International Museum of Surgical Science

Those with stronger stomachs and a love for museum life can head to the International Museum of Surgical Science in Gold Coast. With over 10,000 sq. ft. of galleries committed to the history of surgery from the West and the East, make sure your appetite is filled before hitting the floor. Guests can view some of the earliest X-rays ever taken, blood exhibits, an array of stones — bladder and kidney, not gems — and ancient surgical tools. Visitors also can learn how amputations were performed before anesthesia thankfully found its way to us.

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3. Woolly Mammoth Antiques and Oddities

Why shop on Michigan Avenue when you can head north to a retail store unlike any other? This shop specializes in “amusing and eclectic items resurrected from the past,” according to its website. This includes taxidermy, anatomy items, skulls, bones, specimens and much more. This cultural icon is so famous that the store sells its own internal merchandise like T-shirts, stickers, pins and of course gift cards for Woolly Mammoth frequenters.

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4. Weird Chicago Tours

For those who want to fully immerse themselves in the wacky, Weird Chicago Tours offers an array of tours of both famously-known and off-the-beaten-path places in Chicago. Visitors and Chicagoans alike can tour gangster spots, crime scenes (yes the hunting grounds of John Wayne Gacy are included), haunted historical places — think Murder Castle — and even enjoy a Red Light District Pub Crawl or the Blood, Guns & Valentines Tour. The three-hour tour (hopefully no one gets stranded on the bus) allows tourists to jump off and experience the sights first-hand while being fully engaged in stories based on more than 20 years of research.

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Make Wacky Chicago Your Home

Chicago is a vibrant and beautiful city with dozens of unique neighborhoods and hundreds of housing options. It can be overwhelming to sort through the listings online, many of which are fake, outdated or incorrect. AptAmigo makes the apartment hunt a total breeze by giving you a team of real people who are specifically dedicated to helping you find your dream home. Learn more about how it works here.

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