Uncover 13 unique experiences in Chicago

Chicagois a city celebrated for its blustery weather, deep-dish delights, and an electrifying energy that seems to reverberate off its architectural marvels. But beyond the well-trodden tourist paths lies a world of unexpected adventures. If you're looking for unique experiences in Chicago, don’t worry - you can easily transform a typical visit into a captivating tale.

From venturing below the city's bustling streets to scaling dizzying heights, these hidden gems and exhilarating activities will allow you to experience the Windy City in ways that are anything but ordinary.

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13 unique experiences in Chicago

Here's a list of Worldpackers team's favorite experiences in Chicago:

1. Kayak down the Chicago River

Often praised for its architectural legacy, Chicago's skyline narrates tales of innovation and ambition. This isn’t limited to just looking up though. Kayaking down the Chicago River offers a captivating shift in perspective. Surrounded by towering skyscrapers, you're treated to an immersive journey through an architectural canyon.

The experience allows you to appreciate the city’s intricate designs from a unique vantage point. You can book an architecture tour or rent a kayak and set off at your own pace under historic bridges with Urban Kayaks.

2. See Chicago from above and beyond

But why limit yourself to ground level when you can also witness the cityscape in all its glory from above? Ascend to the iconic Willis Tower observation deck, more specifically The Ledge, and feel your pulse quicken as you stand suspended 1,353 ft above ground level.

Enclosed in a glass box jutting out from the building, you get an unparalleled 360-degree vista of the cityscape and feel as if you are floating among the clouds. Visible are all of the city’s best-known landmarks, including public art pieces in Millennium Park and Navy Pier.

For another equally heart-stopping experience, consider TILT at the 360 CHICAGO Observation Deck on the 94th floor of the John Hancock Center.

3. Celebrate art beyond museum walls

Chicago’s artistic spirit goes beyond the polished halls of its world-renowned museums. This vibrant city is home to a constantly growing and evolving street art scene, with expressions painted across buildings and tucked into alleyways across Chicago.

These artistic treasures tell stories of history, culture, and social commentary. Seek them out while strolling through neighborhoods like Pilsen or Wicker Park. Or take an organized tour to dive deeper into the artists and meanings behind the works.

We suggest checking out the “Offbeat Street Art Tour of Chicago”. This tour guides you through some hidden artistic gems and gives a real understanding of the inspiration and narratives behind these incredible murals.

4. Marvel at the largest permanent digital art projection in the world

Even more impressive are the enormous Art on theMART projections you’ll see displayed on the river façade of the Merchandise Mart along the Chicago Riverwalk. 

As the largest permanent digital art projection in the world, Art on theMART bathes the 25-story building in constantly changing art displays, free for all to see. Visible along the Riverwalk between Wells and Franklin Streets, this impressive display of public art is certainly worth a visit.

5. Dive into the heart of musical heritage

The essence of music permeates the streets of Chicago, a city renowned for its jazz and blues. And the traces of Chicago's vibrant musical era from the early 1900s are still scattered throughout the city, although often overlooked by tourists.

One of our favorite unique experiences in Chicago is going on a Chicago Blues Tour to discover these hidden gems. You can learn about key locations like the birthplace of Chicago blues on Maxwell Street Market, and the legendary Chess Records.

6. Have dinner in a comic book

Remember those days of pouring over your favorite comics, wishing you could step into those colorful panels? Now you can at 2D Restaurant.

This restaurant takes dining to another dimension, with its hand-painted walls creating the illusion of being inside a cartoon world. Delight in savory Asian cuisine, sipping sweet Vietnamese coffee, or biting into a mochi donut. All while feeling like you’ve become part of a black-and-white masterpiece. It's both delicious and totally unique.

7. Embark on a flavor expedition with Pizza City, USA

Chicago is known for its pizza, but there is more than just one style of pizza. This is where culinary creativity flourishes, from thin crust to stuffed to that classic, ooey-gooey Chicago deep-dish.

Steve Dolinsky, a James Beard award-winning writer, guides Pizza City, USA tours. He will take you on a flavor journey to experience a taste of Chicago's different types of pizza. Prepare to have your pizza knowledge blown away. 

After all, the company promises you: “By the end of your tour, not only will you be stuffed with pizza, you will also know first-hand why Chicago is Pizza City, USA.”

8. Magic and mystery at The Magic Parlour

A wave of the hand, a sleight of the wrist... and disbelief washes over you. Dennis Watkins' performance at The Magic Parlour isn't just about pulling a rabbit out of a hat. He crafts an experience brimming with illusion, storytelling, and wit.

In the intimate space, you’re not merely an audience member. You become part of the magic's unfolding. And with Watkins’ mastery, you might just believe that maybe, just maybe, real magic does exist.

9. Explore the hidden wonders of the Chicago Pedway

Beneath the bustling streets of downtown Chicago lies the famed Pedway, an underground network of pedestrian tunnels. Beyond offering a vehicle-free route through the city, the Pedway is very interesting for those looking for a genuine glimpse into local life. Venture into these tunnels to access shops, eateries, and art installations below-ground.

10. Experience the magic of The Chicago Theatre

A visit to The Chicago Theatre offers a journey into a world of elegance and grandeur. Opened in 1921, this iconic venue captures the spirit of classic architectural wonders, drawing inspiration from the Royal Chapel at Versailles. Its remarkable design features create an atmosphere of opulence and sophistication.

The theater has retained its majestic charm over the decades, with its air filled with the excitement and anticipation of preshow moments. Attending a performance here evokes the energy of many other legendary acts that have taken place there over time.

11. Find a quiet haven within Chicago’s hustle and bustle

Looking for a break from the city chaos? Step into a lush jungle paradise - that’s The Garfield Park Conservatory. Imagine wandering through 12 acres bursting with colorful flowers and vibrant plants housed under a gorgeous glass dome.

Breathe in the scent of lilies, gaze at towering tropical trees, and for a few moments, imagine you're worlds away from city sounds.

12. Unwind with an ancient ritual at AIRE's Ancient Baths

Sometimes you need something more luxurious than a stroll through nature. Consider this unique experience for ultimate relaxation: immerse yourself in a piece of history at AIRE's Ancient Baths.

Located in a restored 1902 factory, their concept recreates ancient Roman, Greek, and Ottoman traditions. There, you can bathe in pools of varying temperatures while being surrounded by warm stone. Gentle music creates a calming atmosphere and you'll feel like you're being transported back in time.

13. Pedal or stroll through the Lakefront Trail

What better way to embrace Chicago's lakefront beauty and see the city at your own pace? This 18-mile trail offers an epic, car-free journey through parks, along sandy shores, always with stunning views.

The Lakefront Trail stretches north and south, offering something for everyone, from quiet reflection to a high-intensity workout. You can join bikers, walk around taking in the art installations or simply solace by the water's edge.

Find more unique experiences in Chicago with free stay

If you're dreaming of experiencing Chicago in an authentic, budget-friendly way, Worldpackers is your perfect travel companion. This global platform connects travelers with hosts offering volunteer opportunities, allowing you to exchange your skills for accommodation and other perks.

By volunteering, you can stay in Chicago for free and immerse yourself in local culture, discovering hidden gems and activities beyond the usual tourist attractions. This cost-effective approach also allows you to extend your stay, giving you more time to explore Chicago's diverse neighborhoods, rich history, and cultural offerings.

Chicago is a city full of surprises, and by volunteering there through Worldpackers you might discover hidden jazz clubs, unique art galleries, cozy coffee shops, and scenic parks. Engaging with locals provides insider tips and recommendations, ensuring you experience the city like a true Chicagoan.

For more information on this type of trip, read our full guide on How Worldpackers works.

Worldpackers volunteering experiences are available all around the US and the world and can take many forms, from helping at local nonprofits to welcoming hostel guests. 

Check out one of the volunteering opportunities in Chicago:

Help out with guest relations at a guest house

Tasks include orienting guests to their rooms, hearing any complaints and suggestions of improvement, and housekeeping. In exchange, you’ll get free accommodation, breakfast, lunch, bikes at your disposal, use of an equipped kitchen, fast internet access and a dedicated workspace.

“Truly a unique experience! I always felt like if I was home. Mary is an excellent host. She has a remarkable sense of responsibility and leadership. In spite the fact that she's working 24/7, she is always making sure that all the volunteer and guests needs are taken care of. The tasks at the house are really simple and can be done in a very short period of time, leaving you plenty of time to relax before, during and after your shift. the hostel is located in a friendly, quiet neighborhood and is 15 minutes away from Harlem subway station, which takes you directly to downtown Chicago”, said Diana, from Mexico, who recently volunteered there.

Feel like giving it a try? Click here to see all the information and apply.

Now you’ve had a glimpse of why exploring Chicago goes beyond deep-dish pizza and towering skyscrapers, right? Whether you’re there for just a few days or decide to immerse yourself by volunteering with Worldpackers, dig beneath the surface and embrace the offbeat. It’s here that Chicago reveals itself. Enjoy!