Why go
Chicago pairs world-class architecture and museums with a long, open lakefront. Summer festivals and neighbourhood food make it a great city break.
What to pin
01Architecture river cruise The best way to understand the city's skyline.
02Millennium Park Cloud Gate and the gardens, next to the Art Institute.
03The Lakefront Trail Walk or bike along Lake Michigan's beaches and parks.
04Deep-dish and a ballgame Classic pizza, and Wrigley Field in season.
Where to stay
The Loop for sights, River North for dining, or near the Magnificent Mile for shopping.
When to go
May to October. Winters are cold and windy.
Ideal pace
Plan for 3-4 days. Travel slowly enough to notice where you are instead of racing through a checklist.