Quirky and Unique Experiences in Chicago

Quirky and Unique Experiences in Chicago

Chicago is a truly interesting city and one that tourists flock to. But with 77 city districts—and that’s not counting the little neighborhoods within each of them—it can be a little difficult for a newcomer to find their way around.

Each different neighborhood has its own distinct feel and trademarks. For example, the Gold Coast is where you can rub elbows with Chicago’s elite and max out your credit cards in their high-end shopping district. Lakeview boasts the famous Wrigley Field and The Loop is Chicago’s booming business center, while Lincoln Park is right on Lake Michigan and Andersonville is the place to go if you’re into history and want to see some awesome Swedish construction from the 1800s.

While you’ve probably heard about the typical Chicago tourist spots like Millennium Park and Navy Pier, there are a lot of hidden attractions and restaurants that are worth your while. Dig deep on your trip to Chicago and explore some places that you aren’t going to find in that travel guide you brought.

Before you go, you might want to do some research on the neighborhoods and see which ones have stuff that you’d be interested in. Some of them might be more your style than others, and you can choose which ones to skip to leave time for the rest of the stuff you want to see. Doing your research can really help you make your trip the best it can be.

Ping Tom Memorial Park

While its pagoda is known as a place to catch a Chicago water taxi, the park has a lot more than that to offer. It houses some awesome views of the cities from the rooftop Skyline Patio, has urban kayaking rentals and a field house and ball field.

The park has a bunch of events occurring, especially in the summer that you should be sure to check out. There are some unique cultural ones like the Yin He Dance Company presenting Dance to China. It’s a new way to be exposed to Chinese culture—through dance.

Woolly Mammoth Antiques And Oddities

If you’re looking for weird, Woolly Mammoth is the place to go. According to their website, they specialize in odd, amusing and eclectic items. From taxidermy to toys and skulls to the suspiciously named specimens, you’re sure to find something unique to take home with you. If you have someone back home begging for a souvenir, get them something from here just to see their reaction when they expected a t-shirt with the Bean on it.

Room 13

What’s cooler than a secret speakeasy? Room 13 under the Old Chicago Inn is a password-protected speakeasy where you have to dress the part to get in. It takes you back in time when you walk in, with Prohibition-era cocktails that only include booze from the 1920s and old slot machines.

Apparently you can get the password if you’re a guest at the hotel or you can apply for a yearly membership. The only other way you can get in is if you’re the guest of a member. Good luck!

Division Street Russian And Turkish Baths

This bathhouse originally opened in 1906 in the Wicker Park neighborhood. In 2011 it underwent carful renovation to add more services and modernize, but still keep the history and charm that it had in the beginning. It’s one of only a few bathhouses left in the United States.

After you have a stint in the traditional Russian hot room, you have a chance to try some traditional Russian cuisine in their restaurant. If you’re feeling ambitious, try a plaitza given by one of their attendants—a thorough scrub with a birch broom or a bundle of leafy twigs.


Tucked in below Pops for Champagne, Watershed is a great place for craft beers and artisanal spirits. It’s got a unique menu of drinks and a casual atmosphere that’s different from a lot of other bars. Inside, it basically looks like a living room and things are cozy instead of loud and in your face.

Carroll Avenue

This street runs under a bunch of buildings in Chicago’s River North. This is all that remains of an old freight corridor that brought traffic to the Kinzie Street Bridge. While some of it has been converted into parking lots, and other areas are used for deliveries and garbage pickup, it’s an awesome place to explore. Hidden and abandoned areas are always good spots to check out and it’s interesting to see what’s become of things from the past.

Chicago is filled with hidden gems, but this is a good list to dip your toe in the water. Don’t limit yourself to the things you hear about on TV. Explore everything you can and have something to tell your friends about that they never knew existed.

Kacey HeadshotKacey is a lifestyle blogger for The Drifter Collective. Throughout her life, she has found excitement in the world around her. Kacey graduated with a degree in Communications while working for a lifestyle magazine. She has been able to fully embrace herself with the knowledge of nature, the power of exploring other locations, cultures, and styles, while communicating these endeavors through her passion for writing and expression. Her love for the world around her is portrayed through her visually pleasing, culturally embracing and inspiring posts. Follow her on Twitter, Pinterest and Instagram.