Why go
The skyline is the attraction. A boat tour along the Chicago River is the best introduction to it, and the buildings make more sense once someone has explained them from the water.
The Art Institute holds one of the strongest collections in the country, the lakefront path runs for miles, and the city's blues and jazz clubs are still going strong.
When to go
May to October. Summer brings festivals, beaches on the lake and long evenings. September is often the sweet spot: warm, clear and less crowded. Winters are cold and windy, though hotel rates drop sharply.
Where to base yourself
The Gold Coast and the Magnificent Mile are the classic choice for grand hotels and shopping. River North is closer to galleries and nightlife. The West Loop is where much of the best cooking is, and suits travellers who plan their days around dinner.
What we would build into your trip
A private architecture walk in the Loop, a table at one of the West Loop's tasting-menu restaurants booked well ahead, and a half day in Oak Park for Frank Lloyd Wright's home, studio and the houses around it.
Good to know
Distances are larger than they look on a map. Taxis and the elevated trains are easy to use, and a car is more trouble than help in the centre.