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Unique Things to Do in Chicago, Illinois

There are plenty of guides sharing the main things to do in ”the windy city”, but in this article I want to share some more unique experiences in Chicago.

Chicago is such an interesting city and one that tourists flock to. However, 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.

Before you go, you might want to do some research about the neighborhoods of Chicago and see which ones you’re interested in.

Doing your research really helps make your trip the best it can be as some of them might tickle your fancy more than others.

Each 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. Then you have The Loop, which is Chicago’s booming business center and right on Lake Michigan is Lincoln Park.

Andersonville is the place to go if you’re into history and want to see some awesome Swedish construction from the 1800s.

You’ve probably heard about the typical Chicago tourist spots like Millennium Park and Navy Pier, but there are a lot of hidden attractions and restaurants that are worth your while.

So, let’s dive into the more unique and unusual things to do in Chicago. Places that you aren’t going to find in that standard travel guide.

Unique Things to Do in Chicago

1. Ping Tom Memorial Park

Ping Tom Memorial Park, one of the unique experiences in Chicago

What was once a railroad yard is now a beautiful urban park.

The park’s pagoda is known as a place to catch a Chicago water taxi but Ping Tom Memorial Park has a lot more to offer than just that.

The park houses some spectacular views of the city from the rooftop Skyline Patio.

It also has urban kayaking rentals, a fieldhouse, and a ball field.

The park has a bunch of scheduled events, especially in the summer, so make sure to check it out. Some of them are unique cultural activities like the Yin He Dance Company presenting Dance to China. It’s a new way to be exposed to Chinese culture — through dance.

Also Read: The Best Outdoor Activities in Chicago

2. Woolly Mammoth Antiques & Oddities

an unusual place to visit in Chicago
Photo credit: Woolly Mammoth – unique experiences in Chicago

If you’re looking for a weird but interesting attraction, Woolly Mammoth is the place to go in Chicago.

They specialize in odd, amusing, and eclectic items. From taxidermy to toys and skulls, to suspiciously named specimens, you’re sure to find something unique to take home with you.

If someone back home is begging you for a souvenir, get them something from here and see their reaction if they expect a t-shirt with the Bean on it.

3. Room 13

Room 13 hidden bar
Photo credit: Room 13

What’s cooler than a secret bar? Room 13 under the Old Chicago Inn is a password-protected speakeasy where you need to follow a dress code to get in.

You’ll be transported back in time when you walk in because of its Prohibition-era cocktails made entirely from 1920s booze and its vintage 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 a guest of a member. Good luck!

4. Division Street Russian And Turkish Baths

a unique bathouse in Chicago
Photo credit: Bath House Chicago

This bathhouse originally opened in 1906 in the Wicker Park neighborhood. It underwent a careful renovation in 2011 to be modernized and to add more services, but it retains the history and charm that it had at the start.

The Chicago Bath House, as it is now called, is one of only a few remaining bathhouses in the United States.

After having a stint in the traditional Russian hot room, grab your chance to try some of the traditional Russian cuisines in their restaurant.

If you’re looking for unique experiences in Chicago, try a platza given by one of their attendants — a thorough scrub with a birch broom or a bundle of leafy twigs.

The bathhouse offers a sauna, a full bar, massages, spa treatments, and more.

5. Watershed

Watershed bar in Chicago
Photo credit: Watershed

Tucked in below Pops for Champagne, Watershed is a great place for craft beers and artisanal spirits.

It has a unique menu of drinks and a laid-back atmosphere that distinguishes it from many other bars.

Inside, it resembles a living room, and things are cozy rather than loud and deafening.

6. Carroll Avenue

This street runs under a bunch of buildings in Chicago’s River North.

This is all that remains from 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 is still an awesome place to explore.

Hidden and abandoned areas are always a good spot to check out and it’s also interesting to see the current state of things from the past.

7. Graceland Cemetery

the Graceland Cemetery

This isn’t your typical cemetery.

Graceland is the final resting place for some of Chicago’s famous citizens, and the location of some of the city’s most spectacular gravestones and monuments. The Getty Tomb, the most photographed tomb in the US and an official Chicago landmark, is one of them.

A two-foot-diameter stitched granite baseball marks the grave of William Hulbert, the founder of Major League Baseball’s National League.

The Eternal Silence or the Statue of Death and The Crusader are two other important sculptures in this cemetery.

Truly, this provides the visitors with a distinct sense of Chicago, as well as the people who were primarily responsible for transforming the city into the great metropolis that it is today.

8. The Pedway

The Pedway in Chicago
Photo credit: Aaron Volkening

Hidden below the streets of Chicago is one of the city’s best-kept secrets!

The Pedway is a vast network of tunnels, which runs the length of 40 downtown blocks – yet some of the locals don’t even know about it.

As well as being an ideal way to escape Chicago’s infamously temperamental weather in the winter and an expedient way to get between some of Chicago’s main buildings, it is full of shops, restaurants and art exhibitions – including a stained-glass window and abstract art exhibition.

You could easily spend a whole day just wandering around down here.

Adding further to its mystique, its entrances can only be found down stairways marked with signature yellow stars that aren’t always easy to find.

9. Oz Park

a statue of Dorothy in Oz Park
Photo Credit: Norman

Everyone knows the timeless classic The Wizard of Oz but not everyone knows that its writer – L. Fraum Baum – once made his home in Chicago during the 1890s.

Oz Park has been dedicated to his honor and is home to all sorts of weird and wonderful statues depicting characters from his books such as the tin man, the scarecrow, the cowardly lion, and even Dorothy Gale herself.

What’s more, there’s a playground affectionately titled ‘Dorothy’s Playlot’ and a green space known as the ‘Emerald Gardens’.

The magic of Oz lives on in this beautiful park in the Lincoln Park area and is well worth taking a detour to visit.

10. Jane Addams Hull-House Museum

the Hull-House Museum
Photo credit: Hull-House Museum

This museum is both a historical house museum and the supposedly most haunted location in all of Chicago.

Jane Addams was an important social reformer and visitors are free to explore her house to learn more about her through the exhibition found here.

However, the house also has a rather grisly history due to the mistreatment of immigrants in the area prior to Jane Addams’ arrival.

There are rumors of many ghosts haunting its walls. The most terrifying ones are of a woman in white said to patrol the upstairs corridors and the “Devil Baby” – a demonic child believed to have been locked away in the attic.

Dare you investigate for yourself!

 Unique Experiences in Chicago – Conclusions

unique experiences in Chicago

Chicago is filled with hidden gems, and this is a good list to dip your toe in the water.

Don’t limit yourself to the things you hear on TV. Explore everything you can so you can tell your friends about things they never knew existed.

More Things to Do in Chicago

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Unique things to do in Chicago

Author: Auston Matta
Auston runs the blog Two Bad Tourists and is also a freelance writer. His work has been featured in many publications including Attitude Magazine, Edge Media Network, The Houston Chronicle, and ManAboutWorld Magazine.

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