30 Best Things to Do in Chicago, From Iconic Sites to Can't-miss Museums

Planning a trip to the Windy City? Here are 30 of the best things to do in Chicago.

Chicago may not be the city that never sleeps, but there is surely more to do here than you'll have time. Whether it's world class art, a cultural experience, or sports you seek, you'll find it in the Windy City. Here are some of the best things to do in Chicago.

The Art Institute of Chicago

This downtown museum isn't just an architectural gem, it's one of the best art museums in the United States. It's home to famous pieces including Edward Hopper's "Nighthawks" and Grant Wood's "American Gothic," as well as the largest collection of work from artist Claude Monet outside of Paris.

Museum of Science and Industry

This Hyde Park museum is a great place to spend a cold or rainy day. You could spend hours exploring science, technology, nature, and more through its permanent exhibits alone. But do check the schedule for special exhibitions, which can also be a treat.

Aerial view of downtown Chicago with city parks and the lake in view
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Chicago History Museum

Chicago is where Al Capone once played and where Playboy was born. It's a city full of stories to tell, and there's no better place to discover them than the Chicago History Museum.

Field Museum of Natural History

The Field Museum is one of the largest natural history museums in the world, and its permanent collection includes a number of fossils and the remains of Sue, the Tyrannosaurus Rex. Sue is estimated to be 67 million years old and made her debut at the museum in 2000.

West Wacker Drive Skyline in Chicago
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Take an Architecture River Cruise

Chicago is an architecture nerd's paradise. Several buildings here have been designed by world-renowned architects, and there's no better way to see them than from the river.

Go to a Comedy Club

Chicago is where famous comedians including Tina Fey, Chris Farley, and Jim Belushi got their starts. It's a city with several well-known comedy clubs, including the The Second City which gave rise to many faces you may recognize from Saturday Night Live.

See Live Music

Chicago is a live music heaven with a variety of venues that host performers of all genres throughout the year. It also hosts several music festivals each year, including Lollapalooza, Riot Fest, and world-famous blues and jazz festivals.

Aerial view of North Avenue Beach in Chicago, Illinois
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Go to the Beach

Believe it or not, Chicago is a beach town during the summer. Oak Street and North Avenue Beaches are two sandy beaches along Lake Michigan that are close to downtown and will give you the opportunity to bask under both the sunshine and the shadows of the city's skyscrapers.

Willis Tower

Formerly known as the Sears Tower, this towering giant was once the world's largest skyscraper. That may have changed, but its expansive observation deck still offers some of the best views of the city.

John Hancock Building

This building may not be as well known as the Willis Tower, but it's another place for epic city views. There's also a bar, a restaurant, and occasional events like yoga classes.

The Bean

There may be few more recognizable Chicago symbols than this one by sculptor Anish Kapoor. He, however, may call it by its given name, "Cloud Gate." Most visitors and locals, however, just call it "the Bean."

Buckingham Fountain

If you've ever watched Married with Children, this fountain set in sprawling Grant Park at the edge of Lake Michigan is one you're sure to recognize.

Take an Architecture Walking Tour

There are few better ways to experience Chicago's world-famous architecture than on foot. The Chicago Architecture Center offers several different walking tours, including a couple of tours that focus on the skyscrapers that tower high above the city's streets.

Lincoln Park Zoo

This 35-acre zoo, founded in 1868, is one of the oldest zoos in North America. It's also free to visit and hosts an annual holiday lights show.

Go to the Theater

Broadway isn't the only place to catch a show. Chicago has a vibrant theater scene with plenty of shows to choose from — and many of them with lower ticket prices than you might find in New York.

Shop the Magnificent Mile

If you're looking to do some serious damage with your credit cards, look no further than the stretch of Michigan Avenue known as the Magnificent Mile. You'll find a mix of high-end designer stores, sprawling department stores, and more affordable retailers like Marshalls.

Chicago, Illinois: Horizontal shot of the Frank Lloyd Wright Robbie house exterior view, 5757 S Woodlawn Ave, Hyde Park
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Visit a Frank Lloyd Wright House

If you're a fan of Frank Lloyd Wright's work, head to the University of Chicago campus in Hyde Park where you'll find the Robie House. The house, built in the early 1900s as a single-family home, is considered the greatest example of Prairie School design and is among nearly two dozen homes in the area designed by the famous architect.

"Home Alone" House

You'll need a car to get to this house in the Chicago suburb of Winnetka, but if you grew up on "Home Alone," it'll be worth the drive. You'll recognize it the second you pull up, but remember it's a private residence, so you'll have to appreciate it from the outside.

A general view of ice skaters at Chicago's Millennium Park on March 8, 2013 in Chicago, IL.
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Go Ice Skating

Chicago may get cold in the winter, but some activities — like ice skating through Millennium Park — just wouldn't be the same in warmer temperatures. Each winter, the Maggie Daley Ice Skating Ribbon gives Chicagoans and visitors a one-of-a-kind opportunity to glide through the park.

Visit Wrigley Field

Wrigley Field is one of the most charming stadiums in baseball. It's home to the World Champion Chicago Cubs, and if you don't happen to be traveling during baseball season, you can still take a tour.

Visit Soldier Field

The nearly 100-year-old Soldier Field is home of the NFL's Chicago Bears. And even if you're not into football, you might recognize it from the Clint Eastwood movie "Flags of Our Fathers" or from the television show Chicago Fire.

Visit Navy Pier

If you're looking for a day of family fun, head to Navy Pier in downtown Chicago. You'll find plenty to keep yourself and your family entertained here, and can get a truly one-of-a-kind view of Lake Michigan from the top of a Ferris Wheel.

Take a Walk in Oz Park

There may not be a yellow brick road leading to Oz in Chicago, but there is a park that pays homage to the "Wizard of Oz," which author Frank Baum wrote while living in Chicago. Oz Park on the city's north side features sculptures of all your favorites including Dorothy, Toto, and the Tin Man.

Visit the Chicago Theatre

This Chicago institution is worth a visit even if you aren't able to catch a show. It's where you'll find the iconic Chicago marquee, and if you plan ahead, you may find a favorite performer's name in lights.

Old commercial building with statue of liberty frieze on Damen Avenue in Logan Square, a Chicago community on the North Side. No people.
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Explore a Chicago Neighborhood

Chicago is a city of neighborhoods — 77 of them, to be exact. Wicker Park, Bucktown, and Logan Square are worth exploring on the city's north side. On the south side, consider Pilsen and Chinatown. Architecture buffs are sure to appreciate the historical gems they'll find in Old Town.

Eat Your Heart Out

Chicago really is a foodie paradise that offers something for every palate and every budget. From Top Chefs to holes in the wall, you'll find it all here — and more. Be sure to pack your stretchy pants, and remember Chicagoans don't ask for ketchup on their hot dogs.

Art on display at the National Museum of Mexican Art in Chicago
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The National Museum of Mexican Art

This Pilsen museum is an ideal place to immerse yourself in Mexican art and culture without leaving Chicago city limits. It's one of few major museums in the U.S. dedicated to showcasing Mexican, Latino, and Chicano art and culture.

The DuSable Museum of African American History

This Smithsonian-affiliated museum is a celebration of Black culture and pays homage to Jean Baptiste Point du Sable, who is considered the founder of modern-day Chicago. Highlights of its collection include the former desk of investigative journalist Ida B. Wells.

Visit Millennium Park

Millennium Park is located in downtown Chicago near the Lake Michigan shoreline. Its Jay Pritzker Pavilion is a Frank Gehry-designed bandshell that hosts concerts and other public events. It's also home to the Bean.

Visit Grant Park

Grant Park was one of Chicago's first parks, and a portion of it eventually was carved out to create Millennium Park. Grant Park is where you'll find Buckingham Fountain.

Meena Thiruvengadam is a Travel + Leisure contributor who has visited 50 countries on six continents and 47 U.S. states. She loves historic plaques, wandering new streets, and walking on beaches. Find her on Facebook and Instagram.

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