Chicago wears its ambition on its skyline. Birthplace of the skyscraper, home to the finest architecture tour in the country and a food scene that runs from Michelin tables to street-corner hot dogs, the Windy City rewards a well-planned 48 hours.
Day one: the lakefront and the Loop
Start at Millennium Park beneath Cloud Gate — 'the Bean' — then walk the lakefront to the Art Institute, one of the great museums of the world. In the afternoon, take the Chicago Architecture Center river cruise; there is no better way to read a century of American design than from the water, gliding past the Willis Tower and the Marina City corncobs.
Day two: neighbourhoods and heights
Spend the morning in Wicker Park and Logan Square, where the murals, record shops and third-wave coffee define modern Chicago. Ride up to the 360 Chicago observation deck for the tilt over Michigan Avenue, then wander the Magnificent Mile before dinner.
Getting around
The 'L' train is cheap, elevated and iconic — use it. Chicago is a walking city in the warmer months, but its winters are legendary; pack layers between November and March and plan more indoor time around the museums and markets.
