Let’s face it: Chicago winters are just as bad as everyone says they are.
They’re cold, miserable and have a way of turning all our city’s denizens into blubbering old men in tattered bathrobes angrily gesticulating with a coffee mug full of cheap whiskey.
Or you know, something like that.
But if there’s one surefire way to survive these dreaded next few months, it’s to simply pretend it’s summer. And nothing says summer quite like downing a few crafty cocktails while lounging on a super sexy rooftop bar.
Yes — even in December.
Herein: the nine best all-season rooftops in Chicago, from plump fireside couches and igloos to perhaps the only bar in the country with its own curling rink.
Guess it’s time to learn how to play.
Cindy’s Rooftop
We already told you about Happy’s, the holiday pop-up bar located in the Chicago Athletic Association Hotel. By all means, do that. But do not forget about Cindy’s, the hotel’s crown jewel where big, bench-lined firepits and insanely epic views of Millennium Park meet top-notch cocktails and excellent new American grub. Time it right and you can even get some holiday rollerskating in.
www.cindysrooftop.com
Chicago Athletic Association Hotel, 12 S. Michigan Ave.
The J. Parker
When the weather outside is frightful, this 13th floor hotspot is so delightful. While it shares its historic Lincoln Park home with the charmingly retro eponymous hotel, the J. Parker takes on a swankier, more gentlemanly tone. And that goes double during get-cozy season, when the retractable glass roof transforms the space into 360-degree planetarium and the interior cocktail den dims the lights low enough to enjoy the zoo’s annual Christmas lights display as it should be: with a whiskey-spiked hot chocolate firmly in hand.
www.jparkerchicago.com
Hotel Lincoln, 1816 N. Clark St.
DrumBAR
Like a sophisticated cigar bar without the stink, this indoor-outdoor 18th floor forever-classic cocktail joint is blanketed in a warm sea of deep browns, rich golds, creams and touches of kiwi green to keep things interesting. Inside, imbibers nurse sherry cobblers and one-of-a-kind old fashioned variations atop plump leather fireside couches while outdoor adventurers crowd around coffee table-sized firepits, warming their fingers (and their livers) with stiff Irish coffees.
www.drumbar.com
Raffaello Hotel, 201 E. Delaware Pl.
The Up Room
Standing 13 stories in a neighborhood where buildings rarely top the Blue Line, this intimate 35 seat hotel lounge has been charming Wicker Park’s finest with its unobstructed cityscape sights, iconic spire, and chill atmosphere since May, but that doesn’t mean they can’t hang in the cold. Up & Up recently collabed with Dylan’s Candy Bar on a seasonal tipple modeled after every kid’s favorite cupcake: Worms in Dirt, a blend of housemade Irish Cream with Hangar One vodka, Cynar, milk, oreos and, of course, a gummy worm garnish.
www.therobey.com
Robey Chicago, 2018 W. North Ave.
Upstairs at the Gwen
We’re pretty sure this posh fifth-story outpost is the only bar in Chicago — maybe the only bar in the country — where you can play a game of pick-up curling. And if you needed more of an incentive to drop by, its lavish hotel home (stationed inside the Art Deco McGraw-Hill building, no less) serves up inventive sippers like the Cafe Correcto con Cocco, a creamy concoction of rum, housemade espresso cordial, Averna and cocktail milk. If anything, it’ll enhance your curling prowess. Just try not to slip as you sweep.
www.thegwenchicago.com
The Gwen Hotel, 521 N. Rush St.
Boleo
Take a trip south of the border with a visit to this Peruvian-centric 15th floor tropical menagerie. A retractable glass roof and a bounty of much needed greenery lights up the loft-like room while summery shareable dishes like ceviche and empanadas along with creative pisco-based cocktails like the aptly-titled Adulting is Hard, a soul-quenching mix of savory Dictador 12 year rum, two different kinds of piscos, chai-spiced cereal milk and tangy, smoky black lime, will make it feel like summer never left.
www.boleochicago.com
The Kimpton Gray Hotel, 122 W. Monroe St.
I|O Godfrey
This 15,000-square-foot boozy oasis is not only Chicago’s largest rooftop bar, it’s also the only one where you can pop a bottle of $2,400 bottle of Dom in a reservable heated igloo. Add a retractable roof with eye-catching views, a slew of wintery theme nights, craft cocktails, upscale eats like Wagyu steak tartare and maki rolls, and highroller vibe (leave your athleisure at home, fellas) and this might be cuffing season’s greatest date night destination.
www.iogodfrey.com
The Godfrey Hotel, 127 W. Huron St.
Devereaux
Just because this 18th floor lounge revolves around a pristine swimming pool doesn’t mean it’s strictly a summertime hang. On the contrary, during the winter months the pool transforms into a to a sparkling centerpiece, adding to the hotel’s already luxe ambiance. The food and drink, brought to you by the beloved Boka group, are also on point, so head outdoors, settle into a plush patio chair on the heated deck and enjoy the ridiculous Gold Coast views over a smoky, winter-ready Not Your Mom’s Negroni (mezcal, carpano antica, luxardo bitter, tobacco bitters, flamed citrus).
www.devereauxchicago.com
The Viceroy Hotel, 1112 N. State St.
LH Rooftop
Standing at an impressive 22 stories, this riverside architectural icon is not only the tallest on this list, it’s also one of the most welcoming, especially when the temperature drops to bone-chillingly sadistic levels. Come winter, the staff sets up powerful heaters on the scenic top floor and even doles out cushy blankets for the outdoor bound. There’s also two additional indoor levels for cozying up with a bowl of locally-sourced rye berry risotto, loaded with spring pea butter, fiddlehead ferns, mushrooms and freshly harvested herbs, alongside a soothing London Bridge (Campari, scotch, lemon, hard cider).
www.londonhousechicago.com
LondonHouse Chicago, 85 E. Upper Wacker Dr.
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