1. Wisconsin Dells, WI
Driving time from Chicago: Three hours
The waterpark capital of the world—what's not to love? It doesn't matter if the weather is sunny or rainy, though, because this Wisconsin town offers both indoor and outdoor parks. Mt. Olympus is one of the biggest and most popular, with both water and theme park attractions (and rides for the really little ones as well). Those looking to do something a little different can visit MagiQuest in the Great Wolf Lodge to participate in a live-action role-playing game. If the litte ones come up for air long enough to eat, head to Buffalo Phil's, where kids get their food delivered on a train before spending some coinage in a giant arcade. Paul Bunyan's is a fun, themed spot for an all-you-can-eat breakfast.