Things to do in Chicago and around

Chicago's things-to-do hub is organized into categories because the right day here depends heavily on what brought you. Architecture gets its own category rather than a single line, since the river cruise past the Loop's skyscrapers is the activity most first-time visitors book, and knowing which operator and time slot suits you matters more than for most cities. City sightseeing covers Millennium Park's Cloud Gate, the Riverwalk, the Magnificent Mile and Navy Pier. Museums stand apart from ordinary sightseeing: the Art Institute, the Field Museum, the Museum of Science and Industry and the Shedd Aquarium each reward a half-day on their own.

Observation decks group the Willis Tower Skydeck and 360 CHICAGO, both offering different views of the skyline and the lake. Food and drink covers deep-dish pizza, Italian beef and the city's blues and jazz clubs, which get their own category too, since a Green Mill or Buddy Guy's night is a genuine local specialty, not an afterthought. Sports covers the Cubs at Wrigley Field, the White Sox, Bulls, Blackhawks and Bears. Parks and the lakefront cover the Lakefront Trail and the beaches that open each summer. Shopping points to the Magnificent Mile and West Loop's boutiques.

Family groups what genuinely works with children - the Museum of Science and Industry or Millennium Park's fountain - rather than a late blues club. The day-trips category exists because Milwaukee, Starved Rock and the Indiana Dunes sit well outside the city and deserve their own planning. Seasonal content matters as much here as the sights themselves: summer brings festivals and open patios, while winter closes the cruises and rewards indoor museums instead.