Almost everything you want to do is near downtown, and attractions are clustered together, so there's no schlepping toddlers from one end of the city to the other. The city is laid out like a grid (read: less time consulting maps while the kids are darting off in every direction). The "L," Chicago's elevated train, takes you from downtown to Lincoln Park, where you'll find the Lincoln Park Zoo (bonus: It’s free). Millennium Park, part of Grant Park (home of the Art Institute of Chicago), has art installations that both adults and kids can appreciate. Its Cloud Gate, a $23 million polished stainless-steel sculpture nicknamed "the Bean," distorts reflections like a fun-house mirror. Crown Fountain has 50-foot LED screens with slide shows of Chicago citizens' faces; occasionally water shoots out of a spout in the center of the screen so that it appears to be coming from the person's mouth. To top it all off, "Chicago has beaches! That surprises people," says travel adviser Erik Budde. "The city comes alive in the summer."
Where to stay: The Westin Michigan Avenue Chicago (starwoodhotels.com), which is just a short walk from Oak Street Beach.