Lake Michigan, Chicago
Credit: Chris Zoubris / Getty Images

Take in the Chicago skyline this summer at Navy Pier while riding the 150-foot-high Ferris wheel, or relax and sit on the wooden dock along Lake Michigan. "It's truly family entertainment," Lilliefors says. Grab your friends and challenge them to mini-golf, or navigate remote control boats across the water. Whatever you do, make sure to grab a Chicago-style hotdog while you're there. You can walk it off along the Pier's 34 acres.