| |

7 quirky and unique places 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.

Note: The following is a guest post written by Auston of Two Bad Tourists.

And a disclosure: This article contains affiliate links. If you click on one and make a purchase, I (Rachel) will receive a small commission. This will not affect your price.

Chicago skyline: lots of skyscrapers.
Chicago skyline. Photo courtesy of Carole at Berkeley and Beyond.

Before you go, you might want to do some research about the neighborhoods of Chicago and see which ones you’ll be interested in. Doing your research can really help you make your trip the best that it can be as some of them might tickle your fancy more than others. With that, it will be easy for you to choose which of them to skip or to make more time for.

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. 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. Dig deep and explore some unique places in Chicago that you aren’t going to find in that travel guide you just bought.

The sculpture called "The Bean" reflects the people around it and the skyscrapers behind them.
Photo courtesy of Melissa of My Beautiful Passport.

1. Ping Tom Memorial Park

Its pagoda is known as a place to catch a Chicago water taxi but the park has a lot more to offer than just that. It 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.

Ping Tom Memorial Park: 1700 S. Wentworth Ave. Open daily 6:00-22:00. Fieldhouse (home of the Skyline Patio) open Monday-Friday 9:00-21:00 and Saturday 9:00-17:00. Entrance is free, but there may be charges for some activities. Website.

2. Woolly Mammoth Antiques And Oddities

If you’re looking for a weird but interesting attraction, 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 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.

Storefront with Woolly Mammoth top left and a neon image of a mammoth top right. Odds and ends in the windows and also on two chairs either side of the door. One of the most unique places in Chicago.
Photo courtesy of Woolly Mammoth Chicago.

Woolly Mammoth Chicago: 1513 W. Foster Ave. Open daily 12:00-17:00. Website.

3. Division Street Russian And Turkish Baths

Now called 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 retained the history and charm that it had at the start. It is one of only a few remaining bathhouses in the United States.

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

Bath House Chicago: 1914 W. Division St. Open Monday-Thursday 10:00-23:00, Friday 10:00-midnight, Saturday 7:00-midnight, and Sunday 7:00-23:00. Admission $38 with robes, towels and slippers. Treatments are additional. Website.

Use the map below to book your accommodations in Chicago:


4. 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.

Watershed: Below Pops for Champagne at 601 N. State St. Closed for remodeling, but expected to reopen in May or June 2022. Website.

***In this list of tours, you’ll find plenty to choose from that include weird and wonderfully unique places in Chicago!***

5. 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!

The bar, wood with a row of bar stools, shelves with bottles, and a vintage radio mounted behind the bar.
Photo courtesy of Old Chicago Inn.

Room 13: Old Chicago Inn, 3222 N. Sheffield Ave. Open to guests at Old Chicago Inn or members – ask about becoming a member. Cocktail or business casual attire. Website.

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. A truly unique place in Chicago.

7. 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.

A park-like view, with a pond in front an a classically-columned monument on the far shore. A unique place in Chicago.
Photo courtesy of Graceland Cemetery.

Graceland Cemetery and Arboretum: 4001 N. Clark St. Spring and summer hours: Monday-Friday 8:00-18:00, Saturday-Sunday 9:00-16:00. Fall and winter hours: Monday-Friday 8:00-16:00, Saturday and Sunday 9:00-16:00. Free admission. Website.

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. Also look at this listing of the best places for photography in Chicago before you go!

Are there any other unique places in Chicago that you’d recommend visiting? Add a comment below!

About the author: 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. 

Text: 7 quirky and unique places to visit in Chicago! (and the Rachel's Ruminations logo)
Image: the store front of Woolly Mammoth Chicago

My travel recommendations

Planning travel

  • Skyscanner is where I always start my flight searches.
  • Booking.com is the company I use most for finding accommodations. If you prefer, Expedia offers more or less the same.
  • Discover Cars offers an easy way to compare prices from all of the major car-rental companies in one place.
  • Use Viator or GetYourGuide to find walking tours, day tours, airport pickups, city cards, tickets and whatever else you need at your destination.
  • Bookmundi is great when you’re looking for a longer tour of a few days to a few weeks, private or with a group, pretty much anywhere in the world. Lots of different tour companies list their tours here, so you can comparison shop.
  • GetTransfer is the place to book your airport-to-hotel transfers (and vice-versa). It’s so reassuring to have this all set up and paid for ahead of time, rather than having to make decisions after a long, tiring flight!
  • Buy a GoCity Pass when you’re planning to do a lot of sightseeing on a city trip. It can save you a lot on admissions to museums and other attractions in big cities like New York and Amsterdam.
  • I’m a fan of SCOTTeVEST’s jackets and vests because when I wear one, I don’t have to carry a handbag. I feel like all my stuff is safer when I travel because it’s in inside pockets close to my body.
  • Airalo is an e-sim card. You buy it through an app and activate it when you need it. I tried it on my trip to Thailand and it worked just like any other sim card, but without my having to fuss with physical cards.
  • I use ExpressVPN on my phone and laptop when I travel. It keeps me safe from hackers when I use public or hotel wifi.


Never miss the latest travel news, tips, reviews and amazing finds. Sign up for free and be the first to know when I publish something new!

Notify of
Inline Feedbacks
View all comments