The 15 Best Unusual Things to Do in Chicago

Chicago, the Windy City, is renowned for its stunning architecture, deep-dish pizza, and vibrant music scene. But beyond the usual tourist hotspots, a world of unique experiences is waiting to be discovered. Whether you’re splurging or sticking to a budget, flying solo, or looking for fun things to do with your roommates in Chicago, this list has something for everyone.

1. Kayak at Night on the Chicago River

Experience the city lights in a whole new way by kayaking down the Chicago River at night. This is a splurge-worthy adventure that offers a magical view of the skyscrapers lighting up the skyline. Just make sure you wrap up warm because it can get chilly in the Windy City at night!

This is a great activity that you can do with a few people or big parties.

2. Explore the International Museum of Surgical Science

For those with a curious mind, the International Museum of Surgical Science showcases medical artifacts and oddities. Spanning over 10,000 square feet of public galleries, this is a budget-friendly activity that’s both educational and slightly eerie.

3. Catch a Show at The Neo-Futurists

The Neo-Futurists offer an eclectic mix of experimental theater that’s perfect for artsy roommates or friends. Their flagship show, “The Infinite Wrench,” is a fast-paced barrage of two-minute plays that are wallet-friendly and wildly entertaining. Doors are open up to 30 minutes before showtime.

4. Stroll Through Graceland Cemetery

This isn’t just a cemetery– Graceland is an outdoor museum of Victorian funerary art. It’s a serene and contemplative place that’s home to the burials of many different well-known architects, making it perfect for those who appreciate history and art. Not only that, but Graceland Cemetery is free to enter, which is great news for those on a budget.

5. Attend a Secret Supper

Chicago is home to numerous secret supper clubs. These culinary events are a bit of a splurge but offer a one-of-a-kind dining experience in hidden locations around the city, complete with meals and drink pairings. You’ll receive an email announcing the location on the morning of the event.

6. Discover the Magic Parlour

Dennis Watkins’ Magic Parlour at the Palmer House Hilton is an intimate evening of classic magic and mind-reading performed in a historic hotel. It’s expensive but an unforgettable experience.

7. Bike the 606

Once an abandoned rail line, the 606 is an elevated trail and park that provides a unique and exciting perspective of the city. It’s free, making it an ideal activity for budget-conscious explorers who want to see Chicago from a different angle.

8. Visit the Leather Archives & Museum

This museum is dedicated to preserving the history and culture of the leather and fetishism community. It’s a niche and fascinating visit for those interested in subcultures, with a reasonable entrance fee.

Be aware that due to its adult content, this museum only allows entrants who are 18 years of age and over.

9. Explore the Charnel House

Originally a funeral home, the Charnel House is now a venue for avant-garde arts, including theater, music, and dance performances. Prices vary, but if you’re looking for something fun and unusual to do, it’s a unique experience worth the cost.

10. Check Out the Woolly Mammoth Antiques and Oddities

This quirky shop is a treasure trove of the weird and wonderful, from maps and charts to vintage medical equipment. It’s free to browse, making it a fun and budget-friendly activity you can do either solo or with friends.

11. Relax at AIRE Ancient Baths

AIRE offers a luxurious escape with its ancient bath experiences. With full-body massages and holistic rituals underneath glowing candlelight, this is an experience you won’t forget anytime soon. It’s expensive but provides a perfect relaxation day, especially if you’re looking to pamper yourself or impress a loved one in Chicago.

12. Take a Gangster Tour

Dive into Chicago’s notorious past with a gangster tour. It’s an affordable way to learn about the city’s history while exploring neighborhoods like the Gold Coast and Lincoln Park. They get pretty busy, so we recommend you book in advance if you’re interested in this type of activity.

13. Attend a BYOB Painting Class

Bring your favorite bottle of wine and unleash your inner artist at a BYOB painting class. It’s a fun and budget-friendly way to spend an evening, which makes it perfect for groups or solo adventurers.

14. Explore the City’s Underground Pedway

Chicago’s Pedway is a network of underground tunnels and overhead bridges linking over 40 blocks in the Central Business District. Not only is it free to explore– it’s a fascinating and unusual way to navigate the city.

15. Visit the Federal Reserve Bank’s Money Museum

Learn about the Federal Reserve System and see a variety of exhibits that focus on money and economics. It’s an enlightening, free experience that gives a new perspective on the concept of finance.

Wrapping Up

Whether you’re a long-time local or new to the city, Chicago has a wealth of hidden gems to explore. From high-end experiences to budget-friendly adventures, Chicago’s unusual offerings cater to all tastes and budgets. So, grab your friends, or venture out solo, and start exploring the unique side of Chicago!