Chicago River and Skyline Break, 2 Nights

A driver meets you at O'Hare and takes you to your hotel. In the afternoon, the included architecture cruise takes about an hour along the branches of the Chicago River, with a guide explaining how the city rebuilt itself after the great fire of 1871 and went on to raise some of the first skyscrapers. Choose a flight that lands by late morning; if it arrives later, the cruise may need to move to the next day. Most cruises sail from spring to autumn.

Join the open-top bus and build your own day. Step off at Millennium Park for Cloud Gate, the polished steel sculpture locals call the Bean, and the Art Institute next door; ride on to Navy Pier on the lakefront, then along the Magnificent Mile. Finish at the 360 CHICAGO observation deck, near the top of a landmark tower on North Michigan Avenue, where the city and the lake open up below you, best near sunset.

Breakfast and check-out, then the transfer to the airport for your onward flight. Chicago traffic to O'Hare can be heavy at peak hours, so leave good time. If your flight is late, the hotel can hold your bags while you walk the Riverwalk one last time.