Chicago's skyline

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Chicago
The common joke is that Chicago only gets to enjoy two seasons: winter and construction. And if the Second City wins the bid for the Summer Games, those construction projects are about to skyrocket!

But in my book, Chicago is America's most underrated major city. Part of what makes it such a great destination is that it's found a great balance between being laid-back and friendly, and cosmopolitan and cultural. Among the required activities are a visit to the fantastic Shedd Aquarium (which features—get this—a soy-based roof), kayaking on Lake Michigan when the weather is right and a night of comedy at Second City.

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