Rebecca EngelChicago is one of those cities that just clicks with first-time visitors. It’s big and busy, but it’s also easy to get around, full of green space, and right on the shore of Lake Michigan.
You’ve got famous museums, a skyline that shows up in movies, deep dish pizza, and a lakefront that feels more like a beach town than a major city.
There are so many things to do in Chicago that a first trip can feel a little overwhelming. This guide keeps it simple with 17 of the best spots and experiences, mixing the big must-sees with a few local favorites.
Most of them sit close together downtown, so you can knock out several in a day. Here’s where to start.
1. Snap a Photo at Cloud Gate (The Bean)
Cloud Gate, better known as The Bean, is probably the most famous thing to do in Chicago. It’s a giant polished steel sculpture that reflects the skyline, the sky, and everyone standing around it.
It sits in Millennium Park, right in the middle of downtown. Walking underneath it is half the fun, since the curved mirror finish stretches your reflection in weird and cool ways.
Go early in the morning if you want photos without big crowds. It’s free to visit, and the park around it is worth a stroll too.
2. See the Art Institute of Chicago
The Art Institute of Chicago is one of the best art museums in the country, and you’ll spot its famous bronze lions out front.
Inside you’ll find real showstoppers like Grant Wood’s American Gothic and Georges Seurat’s giant dot painting, A Sunday on La Grande Jatte.
Even if you’re not big on art, an hour or two here is worth it. Give yourself time, because the building is larger than it looks from Michigan Avenue.
3. Look Down From the Willis Tower Skydeck
The Willis Tower Skydeck puts you 1,353 feet above the city, and it’s one of the most popular things to do in Chicago for good reason.
The big draw is The Ledge, a set of glass boxes that stick out from the side of the building. Step onto the clear floor and you’re looking straight down at the streets below.
On a clear day you can see four states from the top. Buy tickets ahead of time to skip the longest lines.
4. Catch the View From 360 Chicago
360 Chicago is the observation deck inside the old John Hancock building on the Magnificent Mile. It’s a great second view of the city, this time facing the lake.
If you’re feeling brave, try TILT, a moving platform that leans you out over the street from the 94th floor.
Sunset is the sweet spot here. Grab a drink at the bar and watch the lights come on across the skyline.
5. Spend an Afternoon at Navy Pier
Navy Pier sticks out into Lake Michigan and it’s one of the most visited things to do in Chicago. The Centennial Wheel is the star, a 200-foot Ferris wheel with enclosed gondolas.
The pier is packed with rides, food stands, boat tours, and open space to walk. In summer there are free fireworks on Wednesday and Saturday nights.
It’s touristy, sure, but it’s a fun and easy stop, especially if you’re traveling with kids.
6. Walk the Chicago Riverwalk
The Chicago Riverwalk is a mile and a half path right along the river downtown. It’s one of the most relaxing things to do in Chicago on a nice day.
You’ll pass cafes, wine bars, and taco spots with patios right on the water. It’s also a great place to look up at the architecture from below.
Walking it is free, and it connects easily to the lakefront and Michigan Avenue.
7. Take an Architecture River Cruise
If you do one paid tour in Chicago, make it the architecture river cruise. Chicago is where the modern skyscraper was born, and the river is the best seat in the house.
A guide points out the famous buildings while you float past them, sharing the stories behind the city’s design.
Tours run about 90 minutes and leave from spots along the river and lakefront. The First Lady and the Chicago Architecture Center cruises are both well loved.
8. Eat Real Chicago Deep Dish Pizza
You can’t visit without trying deep dish, the tall, cheesy, pie-style pizza that Chicago is famous for. It’s less a slice and more a knife-and-fork meal.
Classic spots include Lou Malnati’s, Giordano’s, and Pizzeria Uno, where the whole thing got started.
Keep in mind that a deep dish takes a while to bake, so order as soon as you sit down. One pie can easily feed two people.
9. Shop the Magnificent Mile
The Magnificent Mile is the stretch of Michigan Avenue lined with shops, hotels, and big department stores. It’s the main shopping strip and one of the classic things to do in Chicago.
Even if you’re not buying, it’s a fun walk with the historic Water Tower, street performers, and holiday lights in winter.
It runs from the river up to Oak Street, and it puts you close to 360 Chicago and the lakefront.
10. Catch a Cubs Game at Wrigley Field
Wrigley Field opened in 1914, which makes it one of the oldest ballparks in the country. Watching the Cubs here is a real Chicago experience, even if you’re not a baseball fan.
The ivy-covered outfield walls and the old hand-turned scoreboard give it a throwback feel you won’t get at newer stadiums.
The Wrigleyville neighborhood around it is full of bars and food before and after games. Buy tickets early for popular matchups.
11. Meet the Animals at Shedd Aquarium
Shedd Aquarium sits on the lakefront Museum Campus and is home to thousands of animals, from beluga whales to sea otters and sharks.
It’s a great pick for a rainy day or for anyone traveling with kids. The Oceanarium, with its wall of windows facing Lake Michigan, is a highlight.
The Museum Campus also holds the Field Museum and the Adler Planetarium, so you can pair a few stops in one trip. Book a timed ticket to skip the wait.
12. Come Face to Face With Sue at the Field Museum
The Field Museum is one of the best natural history museums anywhere, and its star is Sue, the largest and most complete T. rex skeleton ever found.
You’ll also walk through ancient Egypt, meet lifelike animals, and see gems and meteorites up close.
It’s right next to the Shedd on the Museum Campus, so the two go well together. Plan on at least a couple hours inside.
13. Play Around at the Museum of Science and Industry
The Museum of Science and Industry is the biggest science museum in the Western Hemisphere, and it’s built for hands-on fun.
You can walk through a real captured German submarine, stand inside a giant model heart, and watch a mock tornado spin.
It sits a bit south of downtown in Hyde Park, so it pairs well with a visit to that neighborhood. Give yourself half a day if you can.
14. Relax in Lincoln Park and the Free Zoo
Lincoln Park is the city’s biggest park, a long green stretch along the lake on the North Side. It’s one of the more low-key things to do in Chicago.
The Lincoln Park Zoo is free and open year round, which is rare for a big-city zoo. You’ll see lions, gorillas, and penguins without spending a dime.
The park also has a conservatory, ponds, and great skyline views. It’s a nice break from the busy downtown.
15. Let the Kids Loose at Maggie Daley Park
Maggie Daley Park sits right next to Millennium Park, and it’s a favorite with families. The play garden is huge, with slides, climbing walls, and a pretend pirate ship.
In winter the park has a skating ribbon that winds through the grounds, which beats a plain old rink.
It’s free to walk around, and it connects to the Bean by a curvy pedestrian bridge. An easy add-on to a downtown day.
16. Try a Chicago Dog and an Italian Beef
Chicago takes its street food seriously. A true Chicago-style hot dog comes on a poppy seed bun with mustard, onion, relish, tomato, a pickle, peppers, and celery salt. Just don’t ask for ketchup.
The other local favorite is the Italian beef, thin-sliced beef piled on a roll and dipped in its own juices. Order it wet with hot giardiniera for the full effect.
Spots like Portillo’s, Al’s Beef, and Gene and Jude’s are local go-tos. It’s cheap, filling, and one of the tastiest things to do in Chicago.
17. Hit the Sand at North Avenue Beach
A lot of first-timers don’t realize Chicago has real beaches, and North Avenue Beach is the most popular one. It’s a wide stretch of sand right on Lake Michigan.
In summer people swim, play volleyball, and grab a bite at the boat-shaped beach house. The skyline view from the water’s edge is hard to beat.
The Lakefront Trail runs right past it, so it’s easy to reach on foot or by bike. Pack a towel and make an afternoon of it.
Start Planning Your Chicago Trip
That’s a solid list of the best things to do in Chicago for anyone visiting for the first time. You really can’t go wrong mixing a couple museums, a lakefront walk, a great meal, and one big view from up high.
Most of these spots sit close together downtown, so a long weekend is enough to see the highlights without rushing. Spring through fall brings the best weather, though the museums make winter easy too.
Pick a few favorites, leave room to wander, and you’ll fall for the city fast.
