Fly to Chicago

Set on the shore of Lake Michigan, Chicago ranks among America's great cities, combining landmark architecture, neighborhoods with deep roots and a food culture all its own. This is where the modern skyscraper was born, so a walk around the Loop today amounts to a tour through an open-air museum of 20th-century design.

Downtown revolves around Millennium Park, with Cloud Gate (better known as the Bean) and free summertime concerts at the Pritzker Pavilion. Along the river, the Chicago Riverwalk has become one of the best public spaces in town, lined with places to eat, kayak rental stands and departure points for architecture cruises. The Art Institute of Chicago holds one of the nation's most important collections, from American Gothic to a superb Impressionist gallery.

Every neighborhood has a personality. Logan Square and Wicker Park are home base for indie bands and dive bars, while Pilsen celebrates its lively Mexican-American community through murals and family restaurants. On the South Side lakefront, Hyde Park is where the University of Chicago sits, and the West Loop has become the place to go for serious dining.

Both United and American run big hubs at O'Hare (ORD), which offers nonstops to almost every US city and a wide international network. On the Southwest Side, Midway (MDW) is smaller, often cheaper and dominated by Southwest Airlines. The city shines from May to October, with patios open, busy beaches and a festival nearly every weekend. Winter is truly harsh, though hotels get cheaper.