We’re lucky to call a world-class city that is constantly impressing on a global scale home. Chicago’s events and activities are ever-evolving, offering fresh experiences each season. But it’s the city’s landmarks, public art, bars and restaurants, rooftops and skyline, and world-class museums that consistently provide us with endless opportunities to explore.
Though we won’t lean on clichés like ‘life’s too short’ or ‘carpe diem’, the past few years have been among the most challenging in recent memory. After witnessing our beloved city endure tough times, now is the time to fully embrace all that Chicago has to offer.
Here, we’ve put together a list of unique experiences for both Chicagoans and visitors alike—a true bucket list for anyone ready to explore the Windy City at its best.
Whether you’re a seasoned local or a thrill-seeking visitor, these are the best things to do in Chicago and must-do activities that should be experienced when in the Windy City!
1. Check off Chicago’s iconic landmarks
If there is one thing Chicago is home to it is a range of extraordinary landmarks and public art pieces. For that reason, we’re kicking off with the most predictable recommendation.
Any city-specific bucket list can’t go without mentioning its picturesque postcard attractions and Chicago is one of the most photographed places in the modern world for good reason.
Before you do anything in Chicago make sure to take in its most famed features. Sit mesmerized by The Bean, dance under the spurt of Crown Fountain, walk along Navy Pier, and enjoy the smaller iconic landmarks like The Historic Water Tower, Calder’s Flamingo, and the Picasso Statue.
2. Revel in Chicago’s riverside rooftops
From the streets to the rooftops, equally as famed as its array of landmarks is the Windy City’s sublime skyline. Among its soaring cityscape, numerous rooftops can be found offering exhilarating experiences drinking and dining among the skyscrapers of Chicago. You will struggle to find a more memorable Chicago evening than one spent sipping cocktails under the stars.
Of the many choices, there is always something happening at River North’s vibrant and verdant Joy District rooftop, whilst London House Chicago is a photographer’s paradise known for its stunning vistas of the Chicago River and Michigan Avenue. Though not riverside, a really iconic Chicago photo can be had at Cindy’s Rooftop in the Loop where you’ll find sweeping panoramic views of Millennium Park and award-winning cocktails from a lavish setup.
Read our full guide to Chicago rooftops.
3. Experience live music at The Jazz Room
The Jazz Room transports audiences into the golden age of jazz, soul, and blues; here, professional musicians reimagine classic sounds in an intimate, speakeasy-style setting evocative of 1920s New Orleans. From spirited renditions of Louis Armstrong’s “When the Saints Go Marching In” to soulful tributes of Luther Vandross and heartfelt blues standards, each performance balances carefully curated setlists with spontaneous improvisation, celebrating the roots and evolution of America’s most enduring genres.
Read more about the shows here.
4. Take in the architecture of Chicago on an architecture tour
To truly experience the landmarks, buildings, and skyscrapers that comprise our world-famous concrete jungle and its incredible skyline, an architecture tour should be on every Chicago bucket list.
Be it strolling through the architecture of the Magnificent Mile or being imbued with knowledge at the Chicago Architecture Center, there are plenty of ways to learn all about it.
5. Put your bravery to the test atop Chicago’s sensational skyline
Head up to the Willis Tower Skydeck
Talking of skyscrapers, no trip to Chicago is complete without heading up Sears Tower, more formally known as the Willis Tower. Seeing one of the world’s most famous skylines from the tallest tower in Chicago (and the third tallest in the United States) is a unique and essential Chicago experience. Take a 60-second ride up to the cloud-piercing height of the Skydeck and enjoy unparalleled 360-degree views over our wonderful city.
Millennium Park, Navy Pier, and many of Chicago’s most famous landmarks are all visible from the top making it truly one of the most unique experiences Chicago has to offer. The glass ledge on the 103rd floor allows you to breach the building’s dimensions and stand 4ft outside its walls.
Looking down you’ll see a 1,353 ft drop staring back up at you as you sit in a tiny glass box protruding outside of what was once the world’s tallest building. Equally as impressive in the day as it is at night, it’s not to be missed.
Teeter On The Edge With The Chicago TILT
For another vertigo-inducing experience, on the 94th floor of the John Hancock Center you’ll find the 360 Chicago Observation Deck and the home of TILT.
Dubbed Chicago’s highest thrill ride and the first of its kind in the world, the TILT is an enclosed moving platform that literally tilts you out of the 94th floor. While Willis Tower gets a special mention for its title as the tallest skyscraper in Chicago, the TILT offers a unique Chicago experience you won’t find anywhere else!
6. Kayak down the Chicago River
Back down at a non-nauseating height, there’s a unique way of seeing Chicago from a whole different perspective by taking to the river not aboard an architecture cruise but instead within your own kayak.
Flanked on either side by Chicago’s famous highrise architecture, you can venture through the city’s heart via skyscraper canyons and under historic bridges.
An evening kayak makes for a truly memorable night navigating the waters while the sun sets and the hustle and bustle of the riverwalk activity takes off around you.
Single kayaks, tandem kayaks, and kayaking tours are all available from various operators at both Monroe Harbor and Chicago Riverwalk locations, allowing you to navigate Chicago’s winding river at whichever pace you desire. Learn about the sights with a tour guide or explore the river independently and see where it takes you.
Read more about Chicago experiences with Urban Kayaks.
7. Bike along Lake Michigan
While kayaking, boats, and rooftops offer fantastic ways to see the heart of Chicago, cycling offers a wonderful way to explore the lakefront combining exploration with exercise and should be on every Chicago bucket list.
Cycling has flourished in popularity in recent years and Chicago is consequently becoming more and more bike-friendly.
However much the city changes, The Lakefront Trail will always be an iconic Chicago bucket list experience. Stretching 18 miles from the south of Chicago up to the north you’ll pass harbors, museums, and beautiful beaches, with the city’s sensational skyline on one side and the blue waters of the lake on the other.
Look out for Bike the Drive at the end of May each year when thousands flood the 30-mile stretch of Lake Shore Drive. For all other times of the year Bikes can be easily rented for full days and Chicago’s bike-share program offers over 6,000 Divvy bikes. For newcomers, the Chicago bike tour, known as Bikes, Bites, and Brews takes guests on a bike tour tasting signature Chicago dishes and sampling legendary Chicago craft beer along the way.
Grab tickets to a Chicago bike tour.
8. Skate or climb in Maggie Daley Park
Along with its art, gastronomy, lake, and skyline, Chicago’s plethora of parks and gardens are another source of pride and pleasure. The Loop’s Millenium Park and the connecting Maggie Daley Park are particularly beloved hotspots, In the latter, you’ll find another paramount bucket list experience in Chicago.
Surrounding an incredible climbing wall in Maggie Daley Park winds a public skating ribbon. In the warmer months, it is used as a scooter and rollerblade path whilst in the winter you can experience “alpine in the city” when it becomes an iconic public ice rink and one of Chicago’s most beloved winter-time activities.
The quarter-mile winding ribbon curves up and down around the 40-foot climbing wall twisting, turning, inclining, and declining with the city’s stunning skyline in the backdrop.
Read more about activities at Maggie Daley Park.
9. Experience a gorgeous Candlelight concert
Of all Chicago experiences, few are as enchanting as watching one of the wildly popular Candlelight concerts. The candlelit spectacle is a relaxing yet unforgettable experience that can be found in outdoor and indoor venues all over the city throughout the year.
Flickering candles and melodic sounds combine phenomenally to create magnetic atmospheres in some of Chicago’s most unique locations such as the elegant former Masonic temple and Stan Mansion.
Grab tickets to an unforgettable Candlelight concert.
10. Peruse Chicago’s legendary street art
Today murals do more than just provide an extraordinary spectacle for our eyes. They pay homage to icons, fight for equality, celebrate different heritages, and honor the heroes of society. Chicago’s art scene is another essential experience and with the many talented local artists frequently at work, it is equally as exciting for both tourists and locals alike.
If you’re not familiar with Chicago’s art scene and would like to learn about its history and the inspiration behind some of its famous murals you can head to our article on Chicago’s must-see murals or jump on an Offbeat Street Art Tour of Chicago and be guided by a seasoned street art enthusiast.
Bonus tip: Watch the enormous Art on theMART projections
Another great place to see art in Chicago is on the 2.5-acre river façade of the riverwalk’s Merchandise Mart. Holding the title of the “largest permanent digital art projection in the world”, Art on theMART attracts thousands to the Riverwalk and Wacker Drive in downtown Chicago every week by transforming the 25-story-tall face of the Mart with prismatic moving art projections.
The 30-minute shows run for more of the year with a short winter break before a spring schedule kickstarts an ever-changing run of nightly themed projections. The best places to view the projections are from the jetty section of the Chicago Riverwalk between Wells and Franklin Streets.
Read more about the Art on theMART projections.
11. Bathe in a serene Chicago spa
With the lively pace of Chicago and the array of exhilarating activities on offer sometimes we also need to sit back, relax and unwind. Luckily enough Chicago knows how to do that too and there are an array of idyllic spas and bathhouses in Chicago.
The most unique of these in our opinion has to be, AIRE’s Ancient Baths. Located in a restored historic River West factory dating back to 1902, the baths are inspired by the traditional Roman, Greek, and Ottoman ancient experiences of bathing.
Read more about AIRE Ancient Baths in Chicago.
12. Special Mention: Chicago Skydiving
Now, we’re not saying jump out of a plane in the freezing skies above Chicago straight away, but we are saying give it a go in one of Chicago’s cutting-edge indoor sky diving centers to get a taste of what it is like and why it is such a popular bucket list experience.
With a state-of-the-art iFly Indoor Skydiving Center in Lincoln Park and another iFly Indoor Skydiving Center in Rosemont, Chicago is home to two conveniently located centers where kids and adults can get the same sensation you’d get 12,000 feet up in the sky.
Grab tickets to an indoor skydiving center in central Chicago.
