16 Things to Do in Chicago

Wondering what to do in Chicago? Here’s a list to help you out

If you’re traveling to the Windy City, there are a ton of sights to see. Parks, museums, restaurants, shopping—the list is never-ending. So, where do you start? Check out this go-to guide for the best things to do in Chicago.

1. Take a walk in the park

With more than 7,600 acres of parkland spread across 570 city parks, it’s easy to enjoy the great outdoors in Chicago.

At a massive 1,208 acres, Lincoln Park is the largest public park in the city. Located on the north side, it borders Lake Michigan and stretches 7 miles along the shoreline. Inside, you’ll find museums, nature reserves, sports fields, and even a driving range and golf course.

Another park worth exploring is Grant Park. Occupying 319 acres and bordering Lake Michigan, it’s lovingly referred to as “Chicago’s front yard.” A walk through will lead you to notable landmarks like Buckingham Fountain and Cloud Gate and a number of beautiful gardens and sporting facilities, including a skate park and a dog park. It’s also home to some renowned Chicago-based museums and an aquarium.

2. Spend the day with art

Spanning approximately 1 million square feet, you could easily spend your entire day at the Art Institute of Chicago, the second-largest museum in the country. Marvel at beautiful Renaissance and impressionist artwork before exploring stunning marble sculptures and posing for a photo with the famous bronze lions at the Michigan Avenue entrance.

Over at the Museum of Contemporary Art, you’ll find more than 2,500 works of art in the permanent collection. But this place truly shines when showcasing the latest trends in contemporary art from local and international artists.

A colorful mural with the Chicago skyline in the background.

3. Go back in time

Want to walk back in time and scope out some historic sights? Just head over to the Field Museum®. You’ll find everything from dinosaur bones to mummies to precious gems and geodes. For a truly unique experience, check out the Fossil Prep Lab and see how scientists uncover ancient fossils that have been hidden for millions of years.

4. Catch a movie

The historic Music Box Theatre opened in 1929, and it still has the original exterior and architecture. Featuring a celestial ceiling, the theater was originally built to mimic an open-air Tuscan palazzo. One step inside will have you feeling like you’re outside under the stars, and you can even expect to see some of your favorite film classics.

5. Eat a hot dog

A trip to Chicago simply isn’t complete until your taste buds try a classic Chicago hot dog. And there’s no shortage of restaurants ready to deliver an authentic experience. Famous favorites include the historic Superdawg® drive-in (founded in 1948) and Portillo’s®, a fast-casual Chicago staple.

If you don’t dig on hot dogs, take your palate on a pizza tour of Chicago’s famous deep-dish selections.

A loaded hot dog with fries on the side.

6. Let loose on the water

Lake Michigan might not be a year-round attraction, but consider dinner cruises and boat tours that set sail from the Navy Pier when the weather permits. While you’re there, you can take a ride on the large Ferris wheel and peruse the shops and restaurants along the water.

7. Take in the view

Skyscrapers are no strangers to the Windy City. So, take advantage of the high vantage point and go up. Many of the city’s taller buildings also feature food spots and lounges where you can sit back, relax and look down on the gorgeous Chicago skyline.

8. Shop “the Mile”

The Magnificent Mile is brimming with restaurants, stores and more. If you’re not sure where to stay while you’re in Chicago, this area plays host to a whole bunch of hotels and keeps you central to all of the city’s major attractions, including museums and seasonal activities like ice skating at Millennium Park.

9. Walk your dog

Located in Uptown, some say Montrose Beach is a little less crowded than its neighboring waterside beaches. And unlike the other beaches, you can bring your pup! Volleyball and kayaking are also available. There’s free Wi-Fi if you need to plug in and a nearby nature area if you and your dog want a little escape. It’s a great way to get away from the city without having to travel far.

10. Find peace at the pool

A hidden garden and the relaxing sounds of a waterfall will make your visit to the Lincoln Park Lily Pool a truly serene experience. The pond was designed by landscape architect Alfred Caldwell in the 1930s and restored to its original architectural beauty in the late 1990s. With winding paths and a pavilion surrounding a beautiful lily pool, it’s the perfect place for a book and a picnic.

11. Escape to the Conservatory

Leave the commotion of the city and experience Garfield Park Conservatory. This impressive indoor garden houses thousands of species of plants from across the globe. Inside, temperatures are warm year-round. So it’s a great place to escape the cold. In the warmer months, 10 acres of outdoor gardens are waiting to be explored.

Garfield Park Conservatory in Chicago.

12. Walk along the Riverwalk

Completed in 2016, the Chicago Riverwalk is 1.25 miles long and features a host of photo opportunities, public art and historic buildings. If you’re looking for a more active afternoon, you’ll also find kayaks, water taxis and cycle boats along the way.

13. Visit your favorite animals

Around since 1868, the zoo is home to nearly 200 different animal species. The great ape and bear habitats are guest favorites, and you’ll also find giraffes, pygmy hippos, flamingos and more. The best part? It’s free!

14. Check out a game

Even if Chicago doesn’t house your home team, there’s no arguing that its playing fields are iconic. Whether you’re into football, basketball, baseball or soccer, there’s bound to be a game worth catching.

15. Take one of Chicago’s tours

No matter what you’re into, there’s a tour for you in Chicago. From architecture to art and all of the food you’ll want to eat in between, you’ll find something worth exploring for an afternoon or evening in the Windy City.

The Chicago Theatre at night.

16. Come back for more

There are so many sights to see and experiences to be had that you might find your list of things to do in Chicago getting a little lengthy. Not to worry. There’s enough to go around, and there’s sure to be something for everyone in your group to enjoy. So, take your time. Soak it all in. And if you don’t get to do it all, you can always come back.

We hope you found this helpful. Our content is not intended to provide legal, investment or financial advice or to indicate that a particular Capital One product or service is available or right for you. For specific advice about your unique circumstances, consider talking with a qualified professional.

Related Content