In summer, everyone wants to be in Chicago, and the price of hotel rooms skyrockets. But the entertainment is free once you get there, and it's easy to eat well for very little.
What to do: There's always something free going on at Millennium Park, Navy Pier and Grant Park, including world-class classical music at the Grant Park Music Festival, July 2-Aug. 21.
Events to catch: June 12-13, Old Town Art Fair.
Where to stay: See Where to stay in Chicago.
Details: For more, see Chicago as you like it and Cheap Chicago.