Why now:
Aside from the near-perfect weather in August? Chicago's food scene is having a moment (with a few notable James Beard awards this year to back up the praise).
The 606, an elevated park being compared to NYC's High Line, just opened, and a big new Lagunitas brewery will keep you well hydrated.
Action plan:
Book a stay at the Virgin Chicago, the first hotel from Virgin Air's Richard Branson, or the newly rebooted (and historic) Chicago Athletic Association.
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