Chicago is one of the most dynamic cities in the U.S.—a lively blend of world-class museums, iconic eats, stunning architecture, and that signature Midwestern charm. Whether you’re here for a quick weekend getaway or a longer stay, the Windy City is packed with experiences you’ll love. From legendary landmarks to local faves, here are the can’t-miss things to do in Chicago to make your trip unforgettable.
1. Take an Architecture Boat Tour
Chicago’s skyline is legendary, and the best way to experience it is from the water. A guided architecture boat tour along the Chicago River allows you to admire iconic skyscrapers like the Wrigley Building and Marina City while learning about the fascinating history behind the city’s world-renowned architecture.
For where to eat, stay and play in Chicago, please refer to this post.
2. Explore the Art Institute of Chicago
Home to masterpieces like Grant Wood’s American Gothic and Georges Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, the Art Institute of Chicago is a must for art lovers. Don’t miss its impressive collection of Impressionist and American art.
Pro Tip: Use Big Bus Tours Chicago to drop you off across the street from this and many other Chicago attractions.
Want more Illinois travel ideas? Here are 6 riveting reasons to visit Elgin and 4 more awesome cities to explore in Illinois.
3. Step Onto the Skydeck at Willis Tower
Formerly known as the Sears Tower, the Willis Tower is one of Chicago’s most famous landmarks. Brave visitors can step out onto Skydeck: The Ledge, a glass balcony 1,353 feet above the ground — talk about a photo op!
4. Visit Millennium Park and See “The Bean”
No Chicago trip is complete without a stroll through Millennium Park. The park is home to public art installations, gardens, and summer concerts, but its most famous attraction is Cloud Gate, affectionately known as “The Bean.”
After snapping selfies, you may want to check our guide to where to eat and stay in Chicago for nearby restaurants and coffee stops.
4. Wander Navy Pier
Stretching out into Lake Michigan, Navy Pier is a hub of entertainment. Ride the Centennial Wheel, catch a fireworks show in the summer, or simply enjoy a walk along the pier with sweeping lakefront views.
9. Marvel at the Grant Park Fountain Light Show
In the evenings, head to Grant Park to watch the spectacular light and water show at Buckingham Fountain. It’s one of Chicago’s most photographed landmarks and a magical way to end the night.
6. Stroll the Lakefront Trail
Chicago’s 18-mile Lakefront Trail offers picture-perfect views of the skyline, Lake Michigan, and city beaches. It’s the ideal spot for a morning walk, bike ride, or sunset photos.
There are also Surrey bike riders who can take you there, but always agree on the price beforehand. Be aware that prices may fluctuate significantly.
7. Catch a Baseball Game at Wrigley Field
For sports fans, there’s nothing like cheering on the Chicago Cubs at Wrigley Field, one of the oldest ballparks in Major League Baseball. Even if you’re not a diehard fan, the atmosphere here is electric.
For me, catching the game, eating a Chicago-style hot dog, buying some Cubs merchandise, and getting my iconic Boston ivy photo were the highlights!
8. Laugh Out Loud at The Second City
Chicago is known as the birthplace of modern improv comedy. At The Second City, you can catch hilarious live shows where comedy legends like Tina Fey, Steve Carell, and Bill Murray got their start. There are also snacks, apps, and adult libations for sale, as well as some really cool merch.
10. Discover Science at the Field Museum
Meet “Sue,” the world’s most complete T. rex skeleton, along with countless other natural wonders at the Field Museum of Natural History. This family-friendly museum makes science and history fun for all ages.
Pro Tip: Use the Chicago CityPASS to bundle this and other major Chicago attraction tickets to save lots of money.
I was hosted by the IPW 2025 conference for some of these attractions and also received a Chicago CityPASS and Big Bus Tour tickets to experience a few others. I was not financially compensated for any of these experiences, and as always, all opinions are entirely my own and completely unbiased.