9 Most Unique Things To Do In Chicago (2024)

Sitting Inland in the Midwest, Chicago is an incredible tourism destination. No doubt, by hosting over 50 million visitors every year, the Windy City itself picture its grandness. It has food and culture that will impresses guests no matter from which part of the world they are. It has skyscrapers and a truly picturesque skyline that will never disappoint observers. It has history and heritage that exhibits beautiful tales in a pleasing manner. However, that’s not all where it all ends.

Chicago is a city of off-the-beaten-path gems and unique experiences. Once you look behind the obvious and preached Chicago fun, there are plenty of opportunities to live for. This city is a hub for activities, from the hidden walkways to the mind-blowing shows, free events, best food, and whatnot.

9 Most Unique Things To Do In Chicago

And to explore, enjoy and live them all, we have got some hot travel tips that even the Chicagoans swear by.

1. Devon Avenue

Chicago’s mini-India, Devon Avenue, is a truly culturally rich and aesthetically colourful place. It is one of the biggest Indian, Bangladeshi and Pakistani communities in the west. And if you believe what they say, there isn’t anything this cultural anywhere in north- America’. From saris (Indian traditional dress) to curry, Nalli Nihari (Pakistan’s non-veg delicacy), statues of Hindus Gods, cooking utensils and more, you will discover a world on its own here. While the streets are filled with Bollywood posters, there are always some Hindi and Urdu songs going on in the background. The best time to be here is during South-Asian festivals, be it Deepawali, Holi, Eid, or so on. Make sure you ask for discounts, and they will definitely give.

2. Noble-Seymour-Crippen House

The oldest existing building in Chicago, Noble-Seymour-Crippen House, is a must-visit. It was built back in the year 1833 by Mark Noble as a farmhouse. However, today it serves as a community centre and a historical society museum. Visiting here is like travelling in a time capsule that takes you back to the early 1800s. The Noble House is open only during weekends or if any festival or event is going around. Especially during Christmas, when the entire land is filled with snow blankets and this beautiful grey house is decorated with lights, it is an experience to be here.

3. Go for Chicago Pedway Tours

You may have explored Chicago in endless ways, be it their popular river cruises, city buses, rail hubs or via bike. But have you ever imagined what it feels like walking through a series of underground tunnels? Believe us; it feels extravagance. During summer humidity and winter snow, the Chicago Pedway comes in handy no matter where you are going in the city. Pedway links nearly 40 blocks of Chicago, and unlike the other unmanaged underground tunnels you may have seen, it is extremely well-maintained. If you are a tourist to Chicago, it is one must and unique experience you should try.

4. Do Not Miss The “L” Tour.

One of the unique things to do in Chicago includes opting for the ‘L’ tours. Also known as the Loop tour train, it takes you through the city, offering the best views and observations around. It isn’t a getting somewhere tour but a simple journey in itself. It is history and diversity presented at a very small price. For nearly $3, you can explore the looped pathway of Chicago every single day, which is also cheaper than trains and busses. Exploring the city by train is definitely one different and unique experience of sightseeing.

5. Turtle Racing at Big Joe’s

If it excites your inner child enough, you can be a part of the Turtle race at Big Joe every Friday night. Begin with having your own big meal and drinks at Big Joe and wait until it turns 9 pm on the watch. It is when this honest-to-God reptilian racing begins. Show up a little early to collect your tickets, or else you might miss it. There will be six races with six candidates each. You can bond with your mate turtle and even cheer for him. Don’t worry if he loses the race (it’s a turtle, Afterall); you’ll still get a free drink at the end. Or, if you want to be a part of turtle champions, do come back in November.

6. Chicago French Market

Chicago’s culinary scenes are in no way unique, but if you aren’t the museum or tourist attraction kind of person, it is an experience for you. Chicago French market hosts the biggest and the best culinary scenes of the city every Monday through Saturday. You can try a variety of cuisines like French (the most loved), Chinese, Korean and even Ethiopian. The market gets organized between Washington and Randolph streets dedicatedly at 131 North Clinton. For tourists, it is though a little off loop, but the culinary experience is worth having. Do carry along local money (cash) as not vendor might offer online paying suitability. Also, consider keeping cash in change.

7. Chicago Architecture Foundation River Cruise

Not the most unique but Chicago Architecture Foundation River Cruises are something that Chicagoans cannot stop talking about. There’s isn’t any better way of seeing the iconic architecture of the city than via river cruise. It is basically a 90 minutes tour that takes you through the beautiful Chicago River. The boat features both indoor and outdoor seating, a snack section and a full-service bar. These tours depart from Michigan Ave. and Wacker Dr with their informative staff excitingly telling tales. If, in Chicago, you haven’t experienced the architecture, then your trip is truly missing something.

8. iFLY Chicago (Feel the thrills of indoor skydiving)

A lot of you must have dreamed of skydiving; however, the heights may have come on the way of your courage. Though If you are in Chicago or planning to visit any day soon, keep your fear in the backseat and live your dream. Somewhere within Lincoln Park, the iFLY Chicago offers indoor skydiving opportunities. It does not include free falling from an airplane or fear of opening a parachute; however, the experience builds similarly. iFLY lets you float on a smooth cushion of air with instructors beside you. All you have to carry is a sense of adventure and minimum age of 3. Even though it is a little expensive, it is still worth it.

9. Spend A Night With The Bluest People Around

Another unusual and unique thing to do in Chicago is attending the Blue Man Group festival. Located in the Briar Street Theatre, the event/ festival is all about blue performers. The performance here is all about celebrations of human connection via comedy, art, music, and other non-verbal communication pleasantly euphoric. As the show has been around for years now, millions of people from around the world have been part of the audience. Though it’s not everyone’s jam, if you enjoy simple humour and small details, the show is definitely for you. Make sure you check the schedule well in advance.

We hope that options in our list reads as unique as your expected them to be. Make sure you add at least 4 of them in your Chicago itinerary.