Poet Carl Sandburg once described Chicago as the “city of the big shoulders.” That phrase captures the Midwestern metropolis’ sense of swaggering possibility. This is a place where skyscrapers like the Willis Tower break records, where every neighborhood has its own flavor, where dining culture is defined by Michelin-starred temples of haute cuisine alongside heavy-duty Italian beef sandwiches and deep-dish pizza. From Chicago architecture tours to the city’s museums, from its blues and jazz communities to its theater and comedy scene, the best things to do in Chicago exist on an amplified scale.
Here, get your guide to Chicago’s best attractions, tours, and more.
Summer can bring soaring heat and humidity to Chicago, while winter is when the deep freeze sets in. For a less extreme experience of the Windy City, aim for shoulder season. In the spring, the Cubs return to Wrigley Field. The season is also a great time to visit the Chicago Botanic Garden or the Lincoln Park Zoo. Fall means the return of annual events like the Chicago Jazz Festival and Chicago Marathon.
Chicago is one of the Midwest’s major hubs. Two airports serve the city: O’Hare International Airport and Midway Airport. Metra trains link Chicago to the surrounding suburbs. And the city operates eight “L” rapid-transit train lines, as well as numerous bus lines. Much of Chicago is also bike- and pedestrian-friendly, and easily accessed by taxi. And don’t miss the chance to explore the Chicago River by boat.
Deep-dish pizza is a classic Chicago dish at the top of many visitors’ dining wishlists. But despite its ubiquity, this hearty style of pizza isn't the only option in town. Next time you visit, don’t forget to try the ultra-thin “tavern-style” pizza, which is cut into small square slices. It’s what the locals eat as an everyday staple.
Local Currency US Dollar ($) | Time Zone CST (UTC -6) | Country Code +1 | Language(s) English | Attractions 64 | Tours 444 | Reviews 64,795 |
Born and raised in Chicago, Claire can claim city roots that go back at least three generations. The writer and editor currently calls London her home, but she's still a Chicagoan at heart.
eat—after all, Chicago is a food lover’s paradise. While pizza and hot dogs are a starting point, you can find everything from top-notch Mexican food in Pilsen to exceptional dim sum in Chinatown and Michelin-starred fine-dining destinations around town.
begins with brunch at Lula Cafe in Logan Square (definitely book ahead). After another coffee at Gaslight Coffee Roasters, go for a dose of culture at the Art Institute before cocktails at the Violet Hour ahead of a decadent dinner.
the architectural boat tours, a genuinely great way to admire Chicago’s skyline and coast along the Chicago River. And don't forget deep-dish pizza—while many locals prefer tavern-style pizza, good deep-dish or stuffed pizza is special occasion-worthy.
don’t just stay around the Loop. Chicago is a city of neighborhoods—from Chinatown to Hyde Park, Bronzeville to Humboldt Park, Lincoln Park to Wrigleyville — and the city’s real breadth and scope only come into focus when you leave downtown.
The obvious choice is to head to the 360 CHICAGO Observation Deck in the Hancock Building or the Skydeck Chicago in the Willis Tower. But for fewer crowds, venture to Ping Tom Memorial Park in Chinatown for picture-perfect skyline views.
is assuming Chicago isn’t welcoming. Chicago combines big-city savvy and world-class cultural attractions with a real Midwestern warmth that comes through when you strike up a conversation with locals and listen to their stories.
Downtown Chicago is famous for its architecture—skyscrapers like the John Hancock Center and Willis Tower dominate its skyline (and offer a great view). The best things to do in Chicago include eating deep-dish pizza and touring the city’s world-class museums. And be sure to see its diverse neighborhoods and go sailing on Lake Michigan.
...MoreIf you have just one day in Chicago, start at the Skydeck Chicago at the Willis Tower for panoramic city views. On a walking tour, stroll the Magnificent Mile section of Michigan Avenue. You can also head to Millennium Park to pose near The Bean.” Be sure to try Chicago's famous deep-dish pizza before leaving.
...MoreThe best things to do in Chicago include the attractions of Navy Pier (like the Centennial Wheel ferris wheel). To have fun, head on a boat tour of Lake Michigan or enjoy aerial views at the 360 Chicago Observation Deck. Alternatively, head on a Segway tour of the Lakefront—and even see a Cubs game at Wrigley Field.
...MoreChicago's number-one attraction is Millennium Park. This relaxing green space is just steps from Lake Michigan, and home to many famous public artworks. (The best-known is Anish Kapoor's Cloud Gate,” aka The Bean.) Right next door is the Art Institute of Chicago, where you can continue your cultural immersion indoors.
...MoreSnowy Chicago transforms into a winter wonderland every year. The best things to do in Chicago include discovering the ice rink in Millennium Park or Soldier Field Sledding Hill. Then, warm up in a top-rated museum, like the Art Institute of Chicago or Field Museum. End the evening with a comedy show.
...MoreHome to world-class art, architecture, and cuisine, Chicago is a culture-lovers dream. But knowing where to start as a first-time visitor can feel overwhelming, so exploring the Windy City with a clued-up guide enhances your experience tenfold. Get your guide to present a mix of secret spots and iconic landmarks for the ultimate Chicago intro.
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