16 Best Things to Do for Your Chicago Bucket List
Sky-high views, mouthwatering eats, and music that fills the night–Chicago has a vibe that’s hard to beat.
This city keeps you busy in the best way possible. Here are some must-try things for your Chicago bucket list!
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1. Explore Old Town & Grab Coffee
Old Town’s cobblestone streets and quirky shops feel straight out of a movie, with historic homes and street art around every corner.
The 3 Arts Club Café, tucked inside a stunning glass atrium at RH Chicago, is the perfect spot to chill with a latte under twinkling chandeliers and leafy trees.
2. Marvel at Masterpieces in the Art Institute of Chicago
The Art Institute is home to world-famous paintings like Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.”
Even if you’re not an art buff, it’s wild to see these masterpieces up close.
The museum’s giant lions out front are Instagram stars, and inside, every gallery is packed with color, history, and stories.
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3. Ride the Centennial Wheel at Navy Pier
The Centennial Wheel at Navy Pier is a giant Ferris wheel that lifts you 200 feet above the city. It’s a classic Chicago thrill you can’t skip!
From the top, you’ll catch jaw-dropping views of the skyline and Lake Michigan, especially at sunset when everything glows.
4. Take a Water Taxi to Chinatown for Dinner
Cruise down the Chicago River, watch skyscrapers zip by, and end up in Chinatown, where you can dig into dumplings, noodles, and bubble tea.
The ride is breezy, the food is awesome, and you’ll see the city from a whole new angle.
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5. Snap a Selfie at Cloud Gate
Cloud Gate, better known as “The Bean,” is Chicago’s most famous selfie spot. Its shiny, curved surface reflects the skyline and the crowds, making every photo look wild and different.
People flock here to make funny faces, spot themselves in the reflections, and just hang out on the lawn.
6. Shop & People-Watch on The Magnificent Mile
The Magnificent Mile is Chicago’s most famous shopping street, lined with everything from fancy designer stores to cool candy shops.
Even if you’re not buying, it’s a blast to window-shop and watch street performers do their thing.
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7. TILT at 360 CHICAGO Observation Deck
TILT at 360 CHICAGO is not your average observation deck; the city looks even more epic from up high!
You stand against a glass wall, and then the whole thing tilts outward, giving you a heart-pounding view straight down from 1,000 feet above Michigan Avenue.
8. Stroll the Chicago Riverwalk
The Chicago Riverwalk is a long, winding path right along the river, with cool bridges, public art, and places to grab snacks or ice cream.
You can watch boats glide by, spot kayakers, and see skyscrapers reflected in the water.
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9. Catch a Cubs Game at Wrigley Field
Wrigley Field is one of the oldest baseball stadiums in the country, and seeing a Cubs game there is a total Chicago rite of passage.
The crowd is loud, the snacks are classic, and everyone’s singing “Take Me Out to the Ball Game” during the seventh-inning stretch.
Even if you’re not a huge baseball fan, the excitement in the stands is totally contagious.
10. Relax in Lurie Garden at Millennium Park
Lurie Garden is a hidden gem tucked inside Millennium Park, filled with colorful flowers, buzzing bees, and shady spots to kick back.
The garden is peaceful, and you can spot butterflies and birds while you chill on the grass or stroll the winding paths.
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11. Laugh Out Loud at The Second City Comedy Club
The Second City is where comedy legends like Tina Fey and Steve Carell got their start.
The shows are packed with hilarious sketches and improv, and the comedians often poke fun at Chicago itself.
Every night feels different, and you never know when you’ll spot the next big star.
12. Admire the City from Willis Tower Skydeck
Standing on The Ledge at Willis Tower feels like floating above Chicago. The glass boxes jut out from the 103rd floor, so you’re literally standing over the city with nothing but clear glass beneath your feet.
The views stretch all the way to Indiana and Wisconsin on a clear day, and snapping a photo here is a total badge of honor for any Chicago visitor.
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13. Take an Architecture River Cruise on the Chicago River
Chicago’s skyscrapers are world-famous, and the best way to see them is from a boat on the river.
Guides share wild stories about the city’s past and point out buildings with crazy shapes and cool history.
The breeze, the water, and the city’s reflections make it a chill way to learn and snap photos you won’t get anywhere else.
14. Wander Through the Garfield Park Conservatory
The Garfield Park Conservatory is packed with towering palm trees, giant ferns, and bright flowers–no matter what the weather is outside.
It’s one of the biggest and oldest conservatories in the country, and you can wander through rooms that feel like different worlds.
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15. Watch the Buckingham Fountain Light Show in Grant Park
Buckingham Fountain is one of Chicago’s most famous landmarks, and its evening light and music shows are a total crowd-pleaser.
Water shoots up to 150 feet in the air, and the lights change colors while music plays. It’s a classic Chicago moment that feels both chill and exciting.
16. Explore the Museum of Science and Industry
The Museum of Science and Industry is packed with hands-on exhibits, giant trains, a real submarine, and even a tornado you can control.
There’s always something new to discover. You can touch, try, and learn cool stuff in every corner, making it a must for curious minds of all ages!
