Cindy’s Rooftop Adding Outdoor Terrace Bar With Boozy Popsicles and Rosé

One of America’s best rooftop bars expects to get even better by Memorial Day. Cindy’s, the uber-popular rooftop bar and restaurant on the 13th floor of the acclaimed and restored Chicago Athletic Association hotel in the Loop, is building a new outdoor bar on its terrace overlooking Millennium Park and Lake Michigan. Expect boozy popsicles and ice cream pops, multiple rosé options, a rotating large-format cocktail menu, and more to be available outside when it hopefully opens around mid-May, reps say.

Lines to get into Cindy’s are commonplace outside the elevators in the hotel lobby, and once inside, waits to get drinks are also common for those soaking in the sun and fresh air on its outdoor terrace. Management hopes that the new bar will alleviate waits for those on the terrace — as its being built solely to service those customers outside — in addition to the new drinks and frozen treats that could increase the rooftop’s popularity, if that’s possible.

Pastry chef Jove Hubbard’s creative flavors of boozy popsicles and ice cream bars, which he debuted at a ground-floor popup at the hotel from June until August last summer, should be the highlight of the new bar’s menu. Last year’s flavors, which were often made with chocolate or fruit-shelled ice cream or sorbet with the option to add alcohol, included cara cara dreamsicle, strawberry rosé, machiatto, banana pudding (roasted banana ice cream, white chocolate shell, Nilla wafers), and cherry bomb (amaretto ice cream, white chocolate shell, amaretti cookies).

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Also look for a rotating selection of four rosés curated by sommelier Sterling Knight and group-sized cocktails by “spirit guide” Nandini Khaund. More details on the menu and new bar will be available before it opens.

Chicago’s selection of rooftop bars ballooned in both quantity and popularity the last couple years, and many more promising ones are slated to debut this year. So Cindy’s, perhaps the best of them all, is attempting to up its game this summer too. Stay tuned for more intel.