Thinking about a trip to Chicago? You’re in for incredible food, beautiful lake views, and that lively city pace that makes it hard to sit still.
From taking an architecture cruise on the river to catching a show at The Second City or digging into a slice of deep dish, Chicago delivers a little bit of everything.
I’ve been lucky enough to visit Chicago many times over the years, and am sharing some of my favorite things to do in Chicago in this article.
1. Visit Millennium Park & The Bean
Start your visit at Millennium Park, right in the heart of downtown. You can’t miss Cloud Gate, better known as The Bean; its mirror-like surface reflects the city’s skyline and everyone who walks by, making it one of the most photographed spots in the Midwest.
And while you’re here, don’t just rush through. Take time to walk around the Jay Pritzker Pavilion, and cool off by the interactive Crown Fountain in the summer.
2. Explore The Art Institute of Chicago
Right next to Millennium Park sits one of the world’s greatest museums – the Art Institute of Chicago. You’ll see major works here from Van Gogh to Seurat, along with an incredible range of other iconic pieces.
The museum itself feels like a maze of discovery, with peaceful courtyards and quiet corners perfect for escaping the city noise for a bit. Plan for at least two hours, though art lovers could easily spend half a day wandering through its galleries.
3. Walk The Chicago Riverwalk
Few places capture the beauty of Chicago like the Riverwalk. Stretching for about a mile along the Chicago River, it’s lined with cafés, public art, and unbeatable city views. Watching the reflection of skyscrapers ripple in the water as boats glide by is pure city magic.
4. Take an Architecture River Cruise
If you only splurge on one tour, make it the architecture cruise. Chicago is the birthplace of the skyscraper, and hearing how the city rebuilt itself after the Great Fire is surprisingly fascinating. Guides weave history and humor together while pointing out everything from Art Deco icons to sleek modern towers. Try to sit on the top deck if you can — the views are unmatched. And these tours do happen in winter too!
See Architecture River Cruise tours.
5. Visit Navy Pier
Yes, Navy Pier is touristy…but it’s also undeniably fun. The Centennial Wheel gives you sweeping views of the lake and skyline, and in the summer, the pier hosts outdoor concerts, beer gardens, and fireworks (even in winter!).
Families will love the Chicago Children’s Museum, and adults can relax with a cocktail while watching boats come and go. Visit around sunset, when the city glows golden, and the lake looks endless.
6. Shop The Magnificent Mile
Chicago’s Magnificent Mile is where shopping, history, and architecture collide. This stretch of Michigan Avenue is packed with everything from luxury boutiques to flagship stores, plus landmarks like the historic Water Tower and Tribune Tower.
7. Enjoy The Chicago Food Scene
Chicago’s food scene is a highlight of any trip. Deep-dish pizza is a must-try! Pequod’s is a popular favorite, but Lou Malnati’s and Giordano’s are reliable classics as well.
For something quick, grab a Chicago-style hot dog loaded with toppings (just skip the ketchup). And if you’re looking for upscale dining, the city has plenty of standout restaurants, from Alinea’s inventive tasting menus to the cozy dishes at Russian Tea Time.
8. Take in the Views from Willis Tower Skydeck
For one of the best views in the city, head up to the Skydeck at Willis Tower. Standing 103 floors above the ground, you’ll see as far as four states on a clear day. And yes, stepping out onto “The Ledge”—a glass box extending from the building—is as thrilling (and slightly terrifying) as it looks.
9. Or go to the 360 Chicago Observation Deck for more views!
For a completely different perspective, 360 Chicago offers a panoramic view of Lake Michigan and the skyline from the John Hancock Building. If you’re feeling brave, try TILT, a glass platform that leans you outward from the 94th floor. It lasts just a few seconds but will definitely get your heart racing.
10. Visit Lincoln Park Zoo
Lincoln Park Zoo is one of the few free zoos left in the country, and it’s right in the middle of one of Chicago’s most beautiful neighborhoods. You’ll find everything from lions to penguins, all with the city skyline as a backdrop.
It’s a great low-key morning activity, and in winter, the ZooLights festival is especially charming.
The view from the Shedd Aquarium.
11. Explore Museum Campus
If you’re a museum lover, Museum Campus is paradise. This lakefront area brings together the Field Museum, Adler Planetarium, and Shedd Aquarium, all world-class in their own right. You can spend an entire day hopping between them and still not see it all.
Even if you skip the museums, take a walk along the path by the water. The skyline view from the Adler Planetarium steps is one of the most photographed spots in Chicago, especially at sunset.
12. See a Show at The Second City
Chicago is the birthplace of improv comedy, and The Second City is where it all began. Stars like Tina Fey, Steve Carell, and Bill Murray started here, and the tradition continues with nightly shows that blend sketch comedy and improv.
It’s the perfect way to spend an evening—especially if you want a break from sightseeing. The shows are sharp, funny, and uniquely Chicago. You’ll leave in a better mood than when you arrived.
13. Watch a Game at Wrigley Field
Even if you’re not a baseball fan, Wrigley Field is worth a visit. The energy on game days is contagious, and so much fun. And if you can’t catch a game, take a behind-the-scenes tour to see the press box and dugouts.
14. Enjoy The Lakefront Trail
Spanning 18 miles along Lake Michigan, the Lakefront Trail is one of the best ways to see the city. Rent a bike or take a long walk past beaches, harbors, and skyline views that change with every turn.
Locals use it daily to commute or work out, but it’s also one of the most peaceful ways to experience Chicago.
Need a place to stay in Chicago? Check out available hotels here!