Hip, stylish rooftop bar/eatery at the Chicago Athletic Association Hotel with choice seasonal fare.
"The literal crowning achievement of the massive overhaul to the Chicago Athletic Association a few years back, Cindy’s may not have the tallest view overlooking the Windy City (stares dagger at Sears “Don’t Call Me Willis” Tower), but it’s likely the one that will make you the happiest. For one thing, the sightlines to Millennium Park, The Art Institute, and the like are still killer. For another, the drinks are far better than they need to be given the view (that’ll happen when your bar falls under the purview of veteran spirit guide Nandini Khaund). So snag a Spanish-style gin & tonic made with local Letherbee gin and house-made fennel-calamansi tonic, cool off with a creamsicle blending white chocolate gelato and blood orange sorbet, and know that all those suckers in skyscrapers are peering down at you enviously." [Thrillist]
Rooftop Bar
Website: Cindy's
Address: 12 S. Michigan Avenue, Chicago, IL 60603
Sources: 21 Best Rooftop Bars in America