Frank Sinatra sang about Chicago as a “toddlin’ town,” but today it could be called a toddlers’ town. Sure, it’s a big city, but it’s hard to imagine a friendlier place for families with young children. Most of Chicago’s attractions have a multigenerational appeal, so planning an itinerary is child’s play. Its most famous attraction is the Sears Tower, but after you and the small fry get that bird’s-eye view of the city and Lake Michigan, here are some sights that will hold your interest for the long haul.

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