Chicago
Chicago doesn't try to be New York or LA — it's confidently its own thing. The architecture is world-class (take the river cruise, seriously), the deep-dish pizza debate never ends, and the lakefront feels more like an ocean shore than a freshwater lake. Blues and jazz run through the city's veins, the neighborhoods each have distinct personalities, and Chicagoans are genuinely friendly in a way that catches you off guard.
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Chicago travel FAQ
How many days do I need in Chicago?
3 to 4 days. Day one: the Architecture River Cruise ($45-55, do the Chicago Architecture Foundation one), Millennium Park and Cloud Gate ('the Bean'), and deep-dish at Lou Malnati's or Giordano's. Day two: Art Institute of Chicago ($25-35, one of the world's best museums), walk the Magnificent Mile, and Navy Pier. Day three: Wicker Park and Bucktown for food and shopping, a blues club at night (Kingston Mines or Buddy Guy's Legends). Day four: Museum of Science and Industry, Hyde Park, or a Cubs game at Wrigley Field.
What food should I try in Chicago?
Deep-dish pizza is the obvious one — Lou Malnati's, Pequod's (caramelized crust), and Giordano's are the big names. But don't sleep on Chicago-style hot dogs (no ketchup, ever — try Portillo's or Gene & Jude's). Italian beef sandwiches from Al's #1 or Johnnie's Beef are essential. For modern dining, Alinea is world-famous, but Girl & the Goat and Au Cheval (smash burgers, long waits) are more accessible. The Pilsen neighborhood has incredible Mexican food.
Is the architecture cruise really that good?
It's genuinely one of the best tours in any American city. The Chicago Architecture Center Foundation River Cruise on Chicago's First Lady ($47, 90 minutes) takes you past 50+ buildings with a docent explaining the architectural history. You'll see Marina City (the 'corncob' buildings), the Wrigley Building, Tribune Tower, and modern glass towers. Go in the morning or late afternoon for the best light. Book in advance during summer — they sell out.