The Best Winter Rooftop Bars in Chicago

Overlooking the Art Institute and Millennium Park, Cindy's Rooftop is a former men’s club that’s now one of Chicago’s go-to cocktail joints, thanks to “Spirit Guide” Nandini Khaund. Guests linger into the wee hours for cocktails like the Still Slizzard—and an expectedly fabulous liquor list, including 16 year Lagavulin and 15 year Glenfiddich.

Hidden away on the 4th floor of the sleek glass, Cubist-inspired Godfrey Hotel, I/O is a 15,000-square-foot rooftop lounge where all the furniture is crisp white and the fire pit isn’t the only thing that’s lit. Try the Smoked Vanilla Manhattan—made by the chef in the kitchen, not a bartender—which is best enjoyed under the heat of the lamp-inspired patio heaters.

On the 15th floor of the Kimpton Gray Hotel, Boleo may as well be in the hippest neighborhood in Buenos Aires. The Latin American-inspired boite is the perfect place to tuck into a Peruvian street food-inspired menu (don’t leave without ordering the yucca fries with rocoto aioli), plus cocktails that taste like a two week vacation south of the border (you want the coconut negroni).

GQ magazine once deemed Drumbar—lofted 18 floors above the city—“Best Whiskey Bar.” Thanks to connections with The Scotch Malt Whiskey Society, which curates Scottish tipples, it still delivers (and we love that all cocktails are the same price: $16). Grab an Isle of Arran scotch and take in sweeping views of Lake Michigan—or cuddle up next to the fires, squint, and pretend you’re in an Edinburgh castle.

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With events like Six Dollar Mondays, where you can order everything from a “shot & a beer” to a cheeseburger for just six dollars, plus regular DJ nights, Waydown is…Way Cool. But it’s full price menu is worth every hard-earned penny, with cocktails like the Bird’s Eye (Four Roses bourbon, grapefruit, raspberry, sweet vermouth and angostura), a nod to the bird’s eye view of Chicago you get from the top.

Head to the 13th floor of this 1929 Art Deco office building-turned-hipper-than-thou-hotel (by Grupo Habita) to find Up & Up: arguably among the most beautifully designed lounges in the city, with a terrace for taking in the skyline. Don't miss the Grandma Charlotte’s Secret Recipe cocktail—graham cracker infused Evan Williams, pumpkin syrup and toasted marshmallow.

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The cocktails on the winter menu at Upstairs—on the 5th floor of Chicago’s former McGraw-Hill building, with the original Art Deco exterior by Gwen Lux—is perfect for cold days. The Lux Chocolate cocktail is essentially cocoa infused with grand marnier and topped with whipped cream, the Tea-Groni is a Rishi tea Negroni with cinnamon, delivered toasty; both serve to cozy you up from the inside out.