Chicago is a bustling city known for its vibrant arts scene, diverse culinary offerings, and iconic architecture. You’re probably familiar with iconic landmarks like the Willis Tower or Navy Pier, but there are many unique things to do in Chicago that you don’t want to miss.
Are you visiting the Windy City? Whether you love history, are a bona fide foodie, or prefer to spend time outdoors, many hidden gems found in this wonderful city. Here are 15 unique things to do in Chicago that go beyond the typical tourist traps you see in travel guides.
1. Kayak on the Chicago River
Embrace an adventure by booking a kayak trip down the Chicago River. You’ll see the city’s stunning skyline without sitting on a crowded tour bus.
If you’re visiting Chicago in March, you’ll have an even more profound experience on the river! The city dyes the water green to celebrate the holiday! Paddle down the river and then hit up the bars for a drink afterward.
2. Visit the International Museum of Surgical Science
Tourists may see the Museum of Science and Industry, the Field Museum, and the Art Institute on their list of popular attractions in Chicago. For those looking for unique things to do in Chicago, you don’t want to miss this historic mansion on Lake Shore Drive.
The International Museum of Surgical Science showcases a fascinating collection related to the history of surgery. Exhibits include ancient surgical instruments, paintings, and sculptures that trace the evolution of medical practices through the ages.
3. Explore the Magic Parlour
For an evening of enchantment, book a show at the Magic Parlour. The show is hosted by magician Dennis Watkins and features mind-bending magic and mentalism in a sophisticated setting.
It’s a perfect blend of history, performance art, and mystery. Kids will also enjoy the magical atmosphere of the show.
4. Take the Crime Tour
Chicago is home to notorious mobsters like Al Capone and John Dillinger. Learn more about them by booking a crime tour.
You’ll see historic sites throughout Chicago like the site of the Saint Valentine’s Day Massacre and the tunnels used for bootlegging in the 1920s. The tour bus also shows video clips along the way to bring more context to these famous criminals.
5. Watch a Movie at the Music Box Theatre
The Music Box Theatre, a historic movie theater built in 1929, is an old-school theater that harkens back to the Golden Age of cinema. The theater specializes in independent and foreign films, while also showing modern fare.
Fans of shlocky movies shouldn’t miss the midnight showing of The Room. This famously bad movie, written and directed by Tommy Wiseau, is an interactive experience where the audience shouts lines at the screen and throws spoons in the air.
6. Eat at Carnivale Restaurant
Do you love good food? Are you a fan of Latin fusion cuisine? Don’t miss Carnivale Restaurant, located in Chicago’s West Loop.
The interior of the restaurant is bursting with bright colors and festive vibes. Meanwhile, the menu features authentic dishes from South America, Spain, and the Caribbean. There’s even a viewing window where you can watch the tortillas and other entrees being made by expert chefs.
7. Discover the Oz Park
Follow the yellow brick road to Oz Park. Located in Lincoln Park, this beautiful scenic area is dedicated to “The Wizard of Oz” author, L. Frank Baum, who lived in Chicago.
Oz Park features statues of the story’s beloved characters and beautifully landscaped gardens. It’s a wonderful place for families or anyone looking to enjoy a bit of whimsy and nostalgia.
8. Walk Through the Garfield Park Conservatory
The Garfield Park Conservatory is one of the largest greenhouses in the United States. It offers an oasis with thousands of plant species from around the world. Walk through this living museum for relaxation and learning. It offers a sanctuary away from the urban hustle.
9. Check Out the Charnel House
Fans of live performances should catch a show at the Charnel House. The former funeral parlor was repurposed into an arts venue, featuring avant-garde and experimental performances.
You’ll have a uniquely haunting artistic experience at the Charnel House. The diverse array of performances pushes the boundaries of traditional theater.
10. Enjoy Jazz at the Green Mill
Step back in time with a visit to the Green Mill Cocktail Lounge. This historic jazz club was a frequent haunt of Al Capone, but now it’s a thriving venue with delicious drinks and captivating live performances.
Enjoy live jazz in a setting that retains the glamour and ambiance of the 1940s. It’s the perfect spot for music lovers looking for authenticity.
11. Shop at Logan Square Farmers Market
The Logan Square Farmers Market is not your average farmers market. It focuses on sustainable local agriculture, artisanal baked goods, and gourmet cuisine.
Visitors can taste some of the city’s finest local products in a lively community atmosphere. Bring some of the food back to your hotel for a late-night snack!
12. Go Thrifting on Milwaukee Avenue
Michigan Avenue gets all the credit, but those looking for unique things to do in Chicago should head over to Milwaukee Avenue. This thriving street is known for its eclectic collection of thrift stores and vintage shops.
Spend a day hunting for treasures and unique finds, from retro clothing and accessories to antique furniture and vinyl records. You never know what you will find hidden in these shops.
13. Relax at the AIRE Ancient Baths
For a touch of luxury and relaxation, visit the AIRE Ancient Baths. This spa draws on the tradition of Greek and Roman bathhouses.
Enter a serene escape with various pools, steam baths, and optional massages. At the same time, take in the scenery of the atmospheric, refurbished factory where everything is located.
14. Participate in a Workshop at the Lillstreet Art Center
Engage your creative side at the Lillstreet Art Center. Workshops and classes in ceramics, painting, and photography are always available.
Book your class ahead of time. It’s a fantastic way to learn something new and create something beautiful, whether you’re a seasoned artist or a beginner looking for a fun thing to do in the city.
15. Attend the Chicago Architecture Biennial
Are you interested in architecture? The Chicago Architecture Biennial has exhibitions and installations from top global talents. Visit this museum great to engage with contemporary architectural ideas. You’ll learn how they’re applied in urban spaces around the city.
Visit These Hidden Gems
Chicago is a city of endless possibilities. The hidden gems and unique activities available in the Windy City reflect its rich culture and history.
Don’t miss out on these unique things to do in Chicago. Whether you’re paddling down the river, exploring former mobster haunts, or tapping your foot along to live jazz, there are many hidden gems in Chicago that help create an unforgettable experience.
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Alyssa Serio has been a writer and editor since graduating from Aurora University in 2014. In her free time, she loves reading, playing volleyball, and watching any horror movie (even the bad ones) with her husband.