Top 21: What to Do in Chicago (2025)

Welcome to Chicago! Also known as the Windy City or the Second City, this metropolitan area is a hub of stunning architecture, diverse culinary scenes, and breathtaking views. Not sure what to do there? Then, you’re in the right place!

Museums, history, food, art, architecture, nature…Whatever you’re looking for, the Jewel of the Midwest has it. Read on to discover the best things to do in Chicago, and fill your trip with memories as big as a deep-dish pizza.

1. See Yourself in The Bean at Millennium Park

Located in the heart of Chicago’s downtown loop district, this park is a favorite among locals who love exploring the beautiful gardens, fountains, and public art installations.

The park is also home to the city’s most famous piece of public art: Cloudgate, affectionately known as “The Bean.” Attracting visitors with its fun and interactive metallic surface, it’s the perfect spot for some of the best selfies in the city!

2. Explore the Chicago Riverwalk and Lake Michigan

One of the most delightful areas to stroll outdoors is the Chicago Riverwalk, a promenade located on the banks of the Chicago River, which stretches for 1.3 miles (2 kilometers) from Lake Michigan to the Lake Street area.

There you’ll find charming cafés and restaurants, picturesque views of the city, and enjoy art exhibitions and cultural programs. Without a doubt, one of the best things to do in Chicago!

The Chicago River stems from Lake Michigan, one of the Great Lakes in the US. Don’t miss a chance to see the Windy City skyline and enjoy picturesque views on a lakeside cruise. These trips offer a unique perspective on Chicago’s world-renowned architecture, plus an excellent ambiance as you serenely sail along one of the Great Lakes in the US. Book your lake cruise here, and get in on the fun!

3. Get Spooky at Lincoln Park

A 15-minute train ride north of Millennium Park is Lincoln Park, a wide-open green space famously built on top of a former cemetery. No surprise here, there are plenty of ghost stories about the place.

Feeling brave? Take an eerie ghost tour of Lincoln Park and catch the skyline glittering at night!

4. Explore the Art Institute of Chicago

Art lovers will feel right at home here. The Art Institute of Chicago houses masterpieces from all over the world, but hands down, the real star of the show is Grant Wood’s “American Gothic,” an icon of American identity.

You’ll find everything here, from Japanese prints to ancient Greek sculptures. While exploring, channel your inner Ferris Bueller and recreate the iconic image from the film when you stop in front of Georges Seurat’s “A Sunday on La Grande Jette” on the museum’s second floor.

5. Become a Scientist at the Field Museum

Have you ever wondered what it would be like to stand next to a life-size T. rex? At the Field Museum of Natural History, you can see the world’s most complete T. rex skeleton, Sue! Spend a day exploring 4.6 billion years of history during your visit, and see how you measure up next to an actual dinosaur.

Fun fact about Sue, her skull is actually too heavy to be placed on the skeleton, so on display is a replica. Her real skull is located on the 2nd floor of the museum.

In addition to the thousands of fossils on display, you can visit the World Civilizations Pavilion, which tells you about ancient peoples such as the ancient Egyptians, Mayans, and Native American cultures. The museum also houses exhibitions on evolution, ecology, and biodiversity, as well as galleries dedicated to science and environmental history.

6. Have fun at the Museum of Science and Industry

Chicago’s Museum of Science and Industry, or MSI, is one of the largest and most impressive in the world. Opened in 1933, the museum is known for its interactive exhibits that appeal to adults and children alike.

When you visit, don’t miss the U-505, a German submarine captured in the Second World War, the Coal Mine, a life-size replica of this underground world, or the interactive exhibitions of natural phenomena. Step inside a tornado simulator for a real-life experience!

If you’re excited about visiting the MSI, consider setting aside a whole day to see it, to make sure you get to see and interact with all the exhibits. It’s an ideal plan to do in Chicago with children, and there’s no shortage of interactive installations for everybody to have fun with.

By purchasing the Chicago CityPass, you can visit the Art Institute, the Field Museum, the Museum of Science and Industry, the Adler Planetarium, and the Shedd Aquarium. The Adler, Shedd, and Field Museums are located on the Museum Campus, just a 5-minute walk from each other.

Take a day to visit these three cultural institutions, then put the perfect finishing touch on the day as you take a seat along the grassy area of the Museum Campus for a beautiful sunset against the Chicago Skyline.

7. Chicago Food Tour

Start your adventure into Chicago’s cuisine with this classic food tour! Sink your teeth into Chicago classics like the Italian-style beef sandwich, deep-dish pizza, and a Chicago-style hot dog. Remember to bring your appetite!

Bonus: Are there any fans of the FX series The Bear out there? Yes, chef! The restaurant that inspired the hit show sits on the corner of North Orleans Street with Huron. Swing on by and grab an Italian beef sandwich for a unique experience.

8. Sweet Treats

Chicago is a notable donut destination with several hotspots throughout the city. Check them out on this donut tour, starting at the classic Doughnut Vault, famous for its old-fashioned cake donuts.

In the summertime, beat the heat with this ticket to the Chicago Ice Cream Museum. A feast for the eyes, as well as the stomach, the museum has plenty of interactive exhibits and installations for people of all ages to enjoy.

9. Chicago Architecture Center

If it’s your first time here, our recommendation is to get your feet wet on a classic architecture tour of the city. Make your way through a concrete jungle of skyscrapers for an immersive experience.

For an even deeper dive into Chicago’s architectural scene, check out a guided tour of the Chicago Architecture Center. Helpful commentary will give you a better understanding and appreciation of Chicago’s construction feats.

10. Chicago River Cruise

Hop aboard a Chicago River Cruise for a fresh take on the city! Glide past iconic buildings and hear cool stories about Chicago’s skyline while enjoying great views and photo ops. It’s a fun and relaxing way to see the city from a new angle while admiring the incredible architecture.

11. Willis Tower Skydeck

Located on the 103rd floor of the Willis Tower (the former, and still beloved by Chicagoans, Sears Tower), the Skydeck is one of Chicago’s favorite attractions and a must-see. There, you can enter The Ledge, glass boxes that project out of the tower at a height of over 1,312 feet (400 meters).

On clear days, you can enjoy a panoramic view of up to 49 miles (80 kilometers), and you’ll be able to see four different states: Illinois, Indiana, Wisconsin, and Michigan. Not to mention, of course, a magnificent view of Lake Michigan. If you want to visit the Skydeck, you can buy the Chicago CityPass, mentioned above.

12. 360 Chicago Observation Deck

How about a little adrenaline rush during your visit? At the famous John Hancock Center, visitors can hitch a ride all the way up to the top of the building for an incredible view of the Windy City.

Spend the day at 1,030 feet (314 meers)and see how many architectural icons you can spot from this bird’s eye view above the city with your ticket to the 360 Chicago Observation Deck.

13. Take a Ride on Navy Pier’s Centennial Ferris Wheel

Navy Pier is a lively spot in Chicago’s northern downtown, known for its amazing views and iconic Ferris Wheel. Hop on for stunning, year-round city views from climate-controlled gondolas.

Pro tip: If you’re visiting in the summer, be sure to enjoy the free fireworks show every Wednesday and Saturday evening. A 3-minute walk from the pier is Olive Park. Find a comfy spot on the grass, and take in the incredible skyline view as the sun sets and the fireworks begin.

To get around the many different attractions available, consider a hop-on-hop-off sightseeing bus ticket that takes you to the main attractions throughout the city. Enjoy hassle-free transport from Navy Pier to 360 Chicago and soak up every minute in the Windy City.

Make the experience even more special when you opt for a sightseeing bus tour at night. There’s nothing quite like the Chicago Skyline after dark!

14. Catch a Game at Wrigley Field

An icon of Chicago history, Wrigley Field (the Friendly Confines for locals) is arguably the best venue to catch a game at in Chicago. Plus, it’s a super fun thing to do with the kids.

What brings visitors season after season is the stadium’s overall old-timey feel, manual scoreboard included. Grab a hot dog, put on your cap, and take a seat for a classic American experience.

15. Sit Courtside at the United Center

Did you know Chicago is home to a six-time NBA World Champion team? Or that Michael Jordan called the Windy City home during the height of his career? The Chicago Bulls NBA team calls the United Center home, and it’s conveniently located just west of the downtown area! Grab your game tickets and don’t forget to snap a photo next to the Michael Jordan statue just inside the arena.

Then, once the game is over, take a stroll down Restaurant Row along Randolph Street for a nightcap. The perfect ending to any evening in the Second City.

16. Tour the Iconic Chicago Theater

In the Downtown Chicago Loop, you’ll find the theater district. Home to local venues like the Steppenwolf Theatre Company and the Goodman Theatre, you can catch original productions that showcase up-and-coming playwrights and unique performances.

Along the famous State Street, you’ll find the historic Chicago Theater. This stunning French-Baroque-style theater is loaded with history from the Golden Age of cinema. Learn more about it on a tour of the Chicago Theater, included when you purchase the Go City: Chicago Explorer Pass. Save on other attractions and make the most of your visit to the Windy City.

17. Vibe at the Vic Theater

Chicago’s theater scene is packed with stunning venues, but the Vic Theater really stands out. This five-story, vaudeville-style gem opened back in 1912 and has held up beautifully over the years.

Even though vaudeville isn’t around anymore, the Vic is still going strong as a concert venue and sometimes a movie theater. It’s definitely worth catching a show here—check out the mahogany seats and the Italian marble lobby and staircase that give it a classic vibe.

18. Buddy Guy’s Legends

Buddy Guy’s Legends is the go-to spot for authentic blues in Chicago, owned by the legendary Buddy Guy himself. With plenty of live performances, it’s a must-visit for any jazz and blues fan. To see the man, the myth, the legend himself, be sure to pop in in January when Buddy Guy takes to the stage.

19. Kingston Mines

Kingston Mines is one of Chicago’s oldest and largest continuously operating blues clubs. With two stages featuring nonstop live blues music, it’s a vibrant spot to soak up the city’s rich blues heritage.

20. Indiana Dunes National Park

Just a short hour-and-a-half train ride from downtown Chicago is the latest addition to the U.S. network of national parks: Indiana Dunes. Reachable via Metra (long-distance trains), this state park has thousands of acres of rolling sand dunes and hiking trails, perfect for a beach day, hiking, or bird-watching.

21. Fort Sheridan Forest Preserve

This natural haven is located just an hour’s train ride outside of the Chicago Loop and is the perfect getaway to escape the city. Here, you can enjoy hiking trails, wildlife spotting, and kayaking. With convenient on-site rentals available, this spot is an ideal day trip for the family and a great way to reconnect with nature.

We hope this guide has sparked your excitement for the Windy City! With something unique around every corner, Chicago is ready to surprise and delight you. Come and uncover all the amazing things to do in Chicago with Civitatis!