Chicago has world-class architecture, museums, jazz and blues clubs and a long lakefront path that turns into a beach in summer. It is best from May to October, with a festive December.
Good to know
- The L train connects both airports to the Loop; a Ventra card works on trains and buses.
- Book the architecture river cruise early in summer; it is the best way to see the skyline.
- Winter wind is real; layers and hats are essential from December to March.
Eat this
Places the planner can use
Mark places as a must or something to skip. The itinerary is built only from this list; ★ marks the destination’s highlights.
Seurat, Hopper's Nighthawks and American Gothic in one of the best museums in the country.
The Bean, Crown Fountain and Lurie Garden, with free summer concerts at Pritzker Pavilion.
Glass ledges 1,353 feet up; 360 Chicago offers tilt-out windows and a lakefront view.
90-minute boat tour past the city's most famous skyscrapers with a docent.
Lou Malnati's, Pequod's or Gino's East: thick, buttery and an hour's wait.
Bike or walk along Lake Michigan, with a ferris wheel and fireworks at Navy Pier.
Two classic clubs: blues at Buddy Guy's Legends and jazz at Uptown's 1907 Green Mill.
Sue the T. rex and a world-class aquarium, a few minutes apart on the lakefront.
Mexican-American neighborhood with colorful murals and some of the city's best taquerias.
Historic ballpark with ivy walls; a classic Chicago afternoon.
Wright's studio and the Robie House are among the best places to see his early work.