Poet Carl Sandburg once described Chicago as the “city of the big shoulders,” a phrase that 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 its architecture to museums, its blues and jazz communities to its theater and comedy scene, the best things to do in Chicago exist on an amplified scale.
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. Spring sees the Cubs return to Wrigley Field and makes for ideal conditions for an open-air architectural boat tour, while fall means the return of annual events like Taste of Chicago, the Chicago Jazz Festival, and the Chicago Marathon.
Chicago is one of the Midwest’s major hubs, and the city’s two airports—O’Hare International Airport and Midway Airport—make it easy to reach from a variety of domestic and international destinations. Metra trains link the city to the surrounding suburbs, while the city operates eight “L” rapid-transit train lines, as well as numerous bus lines. Taxis and rideshare services offer another way to get around, and much of Chicago is also bike- and pedestrian-friendly.
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 typically comes 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 61 | Tours 407 | Reviews 49,848 |
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.
Chicago is famous for its architecture—skyscrapers like the Willis Tower and John Hancock Center dominate its skyline, and architectural boat tours chart the Chicago River. The Windy City is also known for its signature bites like deep-dish pizza, its world-class museums, dynamic and diverse neighborhoods, and views overlooking Lake Michigan.
...MoreIf you have just one day in Chicago, start at the Skydeck Chicago at the Willis Tower for panoramic city views. Stroll through the Loop to Millennium Park and pose near "The Bean" before exploring the Art Institute of Chicago. Be sure to try Chicago's famous deep-dish pizza before leaving.
...MoreFor a fun-filled day in Chicago, visit the attractions of Navy Pier, embark on a sightseeing boat tour of Lake Michigan, or head to the 360 Chicago Observation Deck for aerial views. Alternatively, go 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, steps from Lake Michigan, is home to many famous public artworks, including Anish Kapoor's "Cloud Gate"—better known as "The Bean." Right next door is the Art Institute of Chicago, where you can continue your cultural immersion indoors.
...MoreChicago is known for its snowy winters. For a winter-wonderland experience, discover the ice rink in Millennium Park or hit the 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 musical or comedy show.
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