There is an abundance of things to do in Chicago. If you're a local or a frequent visitor to the city, even the most breathtaking attractions can wind up looking a little stale. Lucky for you, we've rounded up 20 unique things to do in Chicago, from the offbeat to the downright strange.
1. Enjoy Free Outdoor Concerts and Art at Millennium Park
The only thing better than concerts and art is concerts and art for free, and that's what you can expect at Chicago's iconic Millennium Park. Located near Michigan Avenue in Grant Park, this outdoor space is dotted with lively art installations featuring everything from a sea of suspended glass bulbs to a life-sized bronze cow.
In the summer, the city hosts a menagerie of talented musical artists for park-goers as they lounge, play, and frolic on the lush green lawn. Doubling as a natural haven in the heart of the city and a beloved gathering space, Millennium Park is a veritable feast for your ears, eyes, and wallet.
Millennium Park is also home to Maggie Daley Park, an entertainment wonderland with mini golf, climbing walls, and ice skating.
2. Discover Constellations at the Adler Planetarium
The closest star is 4.2 light-years away — unless you're in Chicago, where the closest star is a few miles down the road at the Adler Planetarium. This historic science center has brought the wonders of astronomy to Chicagoans since the 1930s.
It remains the community's leading link to the great wide universe outside our atmosphere. Step inside the planetarium's walls for a look at its hands-on exhibits, complete with a centuries-old telescope, a massive timeline of the entire universe, and a genuine spacecraft that will have you gazing up at the stars long after you return home.
Don’t forget to stop by Adler’s gift shop on the way out. Take home shirts, hats, cups — anything that’ll summon outer space in your home as a remembrance.
3. Time Travel at the Field Museum of Natural History
Truth is stranger than fiction, and no place embodies this point more than the Field Museum of Natural History. Home to nearly 40 million artifacts and dozens of permanent exhibits, this impressive collection is as vast as the universe itself, offering visitors a glimpse at everything from meteorite shards to life-sized dinosaur skeletons.
The scope of the Field Museum reflects the cultural and ecological diversity of the surrounding city. Step into the museum's quiet halls and uncover a side of history you've never seen, filled with vibrant plant life, complex biomechanics, ancient civilizations, and more.
4. Behold Panoramic Views of Lake Michigan at Promontory Point
Tucked away inside the 600 acres of Chicago's Burnham Park is Promontory Point, a man-made marvel with a view that's nothing short of spectacular. Designed as part of a series of engineered islands, Promontory Point features a grassy knoll leading into a series of stair-like rock tiers that plunge into Lake Michigan.
The result is a dreamlike lookout point with an unimpeded, 180-degree view of the lake's blue waters against the famous Chicago skyline. Grab a towel and some sunblock, and you're ready for an afternoon out on the rocks at Promontory Point.
5. Immerse Yourself in Musical History With a Chicago Blues Tour
Music lives in the concrete streets of Chicago, home to the jazz and blues of the early 20th century. Today, remnants of the city's musical heyday hide in plain sight, often unnoticed by locals and visitors. Uncover them yourself on a Chicago tour that highlights locations famed for their key role in the bustling blues scene.
Attendees pay a visit to the famed Chess Records, relive the birth of blues on Maxwell Street, and step into the old stomping grounds of music legends.
6. Get a Bird's-Eye View at the 360 Chicago Observation Deck
The majesty of Chicago's skyscraping architecture can be felt looking up from any street corner, but what about looking down? The 360 Chicago Observation Deck shakes up perspectives by offering visitors a panoramic glimpse of the city from 1,000 feet in the air.
On the 94th floor of the former John Hancock Center, viewers can point out famed locations on the Magnificent Mile from up high. While you're there, ring in happy hour at CloudBar and test your mettle on Chicago's highest thrill ride, Tilt. It suspends you over the distant sidewalk for a view that's both terrifying and gorgeous.
The 360 Observation Deck can only be outdone by the Skydeck on the 103rd floor of Willis Tower, one of the tallest skyscrapers in North America.
7. Bask in World-Class Art Collections at the Art Institute of Chicago
Delicate sculptures, ancient artifacts, and intricate portraits — you'll find it all and more at the Art Institute of Chicago. This fascinating collection features works from beloved artists, such as Vincent van Gogh, alongside lesser-known masterpieces and artifacts from across the globe.
All three levels of the AIC are primed for visitor engagement. Its paintings, photos, antiquities, and more offer intriguing historical tidbits that astound all. Step into this treasure trove of art and relics to stretch your cultural understanding of both Chicago and the wider world.
8. Take in Art Installations Along the Chicago Riverwalk
Chicago's bubbling art scene isn't limited to the gallery walls of the museum. To discover hidden gems in Chicago, head for the Riverwalk, a scenic park trail speckled with public displays of creativity.
The city's massive collection of permanent and rotating municipal works highlights local artists and showcases the diverse communities that give Chicago its rainbow of ingenuity. Stroll down the Riverwalk and play seek-and-find with iconic art installations, such as the 10-foot-tall allium plant and murals celebrating the city's history of art deco architecture.
Our Guide for the Perfect Chicago Night!
Planning your Chicago itinerary? Make time for a Cirque du Soleil show while we’re in town!
9. Catch a Show at The Chicago Theatre
A visit to The Chicago Theatre is a lesson in atmosphere. The lavish structure emulates architectural wonders, such as the Royal Chapel at Versailles. It features remarkable design elements like a 60-foot terracotta arch and a sweeping lobby staircase.
Still as grand as it was on opening day in 1921, the air inside The Chicago Theatre is steeped in preshow anticipation and operatic drama. Catching a show here, whether it's one of our performances or a knee-slapping comedy act, evokes the dynamism of legendary acts to grace this stage.
Before or after indulging in the dramatic flair of a live performance, why not delve deeper into the city’s wonders by taking a Chicago walking tour and discovering the rich history and cultural tapestry of the Windy City ?
10. Discover Rare Plants at the Garfield Park Conservatory
Nestled within Chicago's concrete streets is a jungle of a different sort. The Garfield Park Conservatory houses 12 acres of vibrant plant life, thriving in the heart of America's third-largest city. Visitors can traverse the free outdoor gardens and the rooms inside a massive glass-encased greenhouse.
From the prehistoric leaves of the lush fern room to the lily pad lake of Aroid House, it's easy to mistake this verdant utopia for an oasis amidst an industrial desert.
11. Rediscover Your Love for the Modern Day at the Medieval Torture Museum
Art museums are great, but they're often lacking in the torture department. Luckily, the Medieval Torture Museum is here to meet your darkest, most specific fascinations. Measuring over 6,000 square feet, this is one of the largest interactive museums in the country. Every inch of it hosts dastardly devices from an age long passed.
Each diabolical exhibit features reconstructed devices, many of which incorporate genuine equipment preserved from the medieval period.
An army of wax dummies illustrates the horrific capabilities of tools designed to crush, saw, and stretch perpetrators. Visitors can test these instruments for themselves as a helpful audio guide imparts lore about each heinous piece.
12. Cheer on the Home Team at a Pro Sports Game
Local sports teams are legends in any city, but Chicagoans are unmatched in their support. Sit in on a professional game the next time you're in the city. Basketball fans will find themselves awestruck at the United Center, the current home of the Chicago Bulls and Michael Jordan, who remains immortalized in a massive statue outside the arena.
Also at the United Center are the Chicago Blackhawks, who continue to thrill fans with an energy you'll find infectious in the stands.
If you’re a fan of America’s favorite pastime, catch some innings at Wrigley Field.
13. Meet Sea Creatures at the Shedd Aquarium
An undersea adventure is the thing to set your Chicago experience apart from the rest. Balanced on the shores of Lake Michigan, the Shedd Aquarium has brought aquatic life to Chicago since 1930. It's now the third-largest aquarium in the nation.
Visitors will get up close and personal with creatures from waters near and far for a peek into the colorful world beneath the waves. Dive deeper with a guided tour or wander the tanks on your own, petting ancient sturgeon, waving to friendly beluga whales, and observing formidable sharks for an experience that will have you pondering the mysteries of uncharted oceans.
14. Dine Like a Cartoon at Chicago’s 2D Restaurant
Next in our roundup of unusual things to do in Chicago is a restaurant that'll have you melting into the pages of your favorite comic book. 2D Restaurant serves up a delectable array of Asian dishes and desserts for visitors to enjoy inside a hand-painted dining room.
Designed by owner Vanessa Thanh Vu, the scene depicts a stunning Parisian fantasy land, complete with a bubbling claw-foot tub, a cozy library, and a crackling fireplace. Reserve a table, not just for the black-and-white view, but also for the sweet Vietnamese coffee, crunchy chicken sandwiches, and light mochi donuts.
15. Have an Enchanting Evening at The Magic Parlour
Don your evening attire and prepare to be amazed by an illusory performance at The Magic Parlour. Led by third-generation magician and mind reader Dennis Watkins, this fantastic show is one of the highest-rated experiences in Chicago.
Audiences laud Watkins' deftness as he expertly pulls off a series of unimaginable tricks involving everything from duct tape to razor blades. Limited seating means you'll see every trick up close as your sense of wonder soars, leaving just one explanation: It must be real.
16. Find Serenity at the Jackson Park Japanese Garden
For a moment of stillness amidst Chicago's bustling crowds, head to the Japanese garden in Jackson Park. Established in the 1930s to signify the mutual respect between Japan and the United States, the garden rests on a stunning inlet and features a charming passel of plants and ornaments.
Visitors can travel the walking path across dreamy wooden bridges, past waters full of koi and lily pads, and beneath a stretch of budding cherry blossom trees.
Take a rest accompanied by the sound of a small rushing waterfall and gaze up at the garden's crown jewel: a genuine Japanese temple once displayed at the World's Columbian Exposition and now resting in this lush pocket of tranquility.
17. Navigate the Underground Tunnels of the Chicago Pedway
The famed Chicago Pedway is an underground pedestrian way system tucked below the busy streets of downtown. But besides being a vehicle-free way to navigate the city, the Pedway also houses an array of fun secrets waiting to be uncovered.
Head down into the Pedway tunnels for below-ground access to shops, quick-bite restaurants, and art installations scattered throughout. If you're visiting, a trip to the Pedway will give you a true taste of what it's like to be a local in this quirky yet lovable city.
18. Savor Each Bite at Alinea
Alinea is the mind-child of superstar chef Grant Achatz, a Michelin-awarded culinary innovator pushing the bounds of restaurant dining. The restaurant highlights stunning dishes developed using molecular gastronomy techniques for a once-in-a-lifetime meal that elicits a powerful sensory response.
A meal here will present you with dishes descending from the ceiling, flaming centerpieces, and upside-down appetizers that are so out of the box you might mistake the acclaimed restaurant for another show at The Magic Parlour.
19. Snap a Selfie at Cloud Gate (The Bean)
Nothing screams Chicago like a 33-foot-tall silver bean. This massive art installation has attracted tourists and locals to the downtown Loop since its unveiling in 2004. In the heart of Millennium Park, The Bean's reflective surface mirrors the skyline and invites visitors to observe the polish.
As one of the city's most iconic public art pieces, The Bean — designed by Anish Kapoor — is now a beloved symbol of the Windy City, making it a must-see photo-op for your next Chicago venture.
20. Dine with Whimsy at Gullivers Pizza & Pub
The great Chicago pizza debate may never have a true winner, but Gullivers Pizza & Pub remains a fierce contender. Dishing up hot pies to Chicagoans for almost 60 years, Gullivers is famous for its deep-dish pizza, complete with a hearty two layers of cheese.
But locals frequent the spot for its atmosphere as much as its food, with wall-to-wall antiques and an ocean of vintage, stained glass lamps. Stocked with good vibes and good pizza, Gullivers is without a doubt one of the quirkiest places in Chicago to grab a slice. That's exactly what makes it so special.
Get Weird in the Windy City on Your Next Visit
With the activities from this list on your Chicago itinerary, you'll get a deeper view of the city that other travelers might be blind to. These niche museums, next-level eateries, and feats of nature mark the Windy City as one of the most diverse destinations in the country.
Cap off your Chicago visit with a final spectacle, brought to you by our wondrous performers. Applauded worldwide for pushing the boundaries of human entertainment, each of our Chicago shows is a blend of imaginative marvels and daring acrobatics.