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Located along the shores of Lake Michigan, Chicago—the largest city in Illinois and the third largest in the United States—offers a wealth of art, music, historical, and architectural experiences. Culture lovers can stroll through Millennium Park and the Loop to view outdoor art (including the iconic “Bean”), tour world-class museums such as the Art Institute of Chicago, or cruise the Chicago River to see modern landmark gems. To meet the locals, buy a ticket for a ball game; catch some live blues or jazz (both of which have deep roots in Chicago) at a club; or laugh at the comedy acts at Second City, where many top comedians launched their careers.
After being cooped up all winter, Chicago is ready to party when the sun comes out (sometime during May). Summer highlights include the annual Taste of Chicago, Chicago Blues Festival, Andersonville’s Midsommarfest, and the Chicago Air and Water Show. Alternatively, fall brings fewer crowds and brisker weather, perfect for exploring neighborhoods on foot and watching the trees turn colors along the quaint neighborhood streets.
The Chicago Transit Authority (CTA) is your best friend when traveling around Chicago. You’ll see many references to “the Loop,” the circle elevated train tracks that define the city’s downtown area. From there, train lines (both underground and elevated) shoot out to the airport and the nearby suburbs. The CTA also has a robust network of bus lines that make all corners of the city easily accessible. The Loop itself is very walkable, and if you’re there in the dead of winter and your toes are frozen, hailing a cab is a cinch.
The best place for a chargrilled Chicago hot dog after bar closing time (2am) is the Weiner’s Circle in Lincoln Park. The dog is served with a pickle, tomato wedges, chopped onions, sweet peppers, celery salt, and a side of major sass from the counterperson. If you know what’s good for you, never ever ask for ketchup—Chicago is a mustard town.
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....More
If 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....More
For 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....More
Chicago'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....More
Chicago 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....More
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