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A person curling on a rink.
Photograph: Courtesy of The Gwen

The 15 best winter rooftop bars in Chicago to get cozy

Rooftop season lasts all year long thanks to these heated patios, igloos and outdoor fire pits.

Samantha Nelson
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Samantha Nelson
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While some rooftop bars in Chicago close when the temperatures plunge, others get creative to extend the outdoor season into the winter. Hot drinks, fireplaces, curling lanes and over-the-top holiday decorations make it well worth bundling up to take in the skyline views that you can find atop downtown hotels and skyscrapers. There are also indoor rooftop bars and restaurants where retractable roofs, heated igloos and lodges mean you can stay cozy while watching the snow fall. Whether you’re looking for a romantic dinner, a boozy brunch or a fun group gathering, you can soak in the city’s beauty from one of these winterized rooftops.

RECOMMENDED: Discover the best things to do in Chicago this winter

The best rooftop bars open during winter in Chicago

  • Restaurants
  • Loop

Running November 18 through January 28, the fourth annual Rudolph’s Rooftop experience on the 22nd floor of LondonHouse Chicago features holiday-themed hot and cold cocktails and whimsical decor, with plenty of great spots for a festive photo. Book an igloo for a group of up to six people with a $600 minimum tab, or just stop in for a drink from the outdoor bar.

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  • Bars
  • Cocktail bars
  • Streeterville

The massive rooftop at Navy Pier offers seven fire pits so visitors can enjoy its panoramic Lake Michigan views year round. Come for brunch to enjoy bottomless mimosas or relax in the evening by sipping a playful cocktail that can be spiked with CBD for an extra buzz.

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  • Bars
  • Cocktail bars
  • Loop
  • price 2 of 4

Heaters and fire pits keep the rooftop cozy, particularly when you cuddle under a blanket on one of the couches while sipping a hot cocktail. For more protection from the elements, book one of the winter greenhouses and share a bottle of bubbly and a cheese and charcuterie board.

  • Bars
  • Lounges
  • River North

The Godfrey’s rooftop becomes a winter wonderland when the temperatures plunge, featuring clear heated igloos decorated with festive lights that can be booked for groups of up to 10 people indulging in bottle service. Even if you’re not going all out, you can hang out at a booth under the retractable roof or gather around an outdoor fire pit for s’mores and a hot cocktail.

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  • Bars
  • Lounges
  • Lincoln Park
  • price 3 of 4

The 55 seats inside the atrium atop the Hotel Lincoln become more in demand when the weather cools, though you can still sit outside around one of the fire tables. Take in the beautiful Lake Michigan views beneath the retractable roof while sipping bottomless mimosas and Bloody Marys during weekend brunch.

  • Bars
  • Wine bars
  • Loop
  • price 2 of 4

The rooftop space on the 24th floor of Pendry Chicago transforms into a winter garden starting November 3, setting up wooden lodges where groups of up to six can get cozy under blankets on rocking chairs and couches arranged around a firepit. Decorated with lights and evergreens, the cocktail bar will offer a special absinthe-focused menu including tableside drip fountains.

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  • Bars
  • Hotel bars
  • Loop
  • price 2 of 4

Both the indoor space and outdoor terrace of the cocktail lounge on the 26th floor of Virgin Hotels Chicago will be open and heated during the winter. From the end of November through the new year, Cerise will transform into the Hughes Holiday House, paying tribute to John Hughes’ Home Alone and National Lampoon’s Christmas Vacation with themed decor, cocktails and dishes.

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  • Bars
  • Lounges
  • Loop
  • price 3 of 4

Take in the skyline views from 27 stories up through the floor-to-ceiling windows on the enclosed bar at theWit Hotel. You’ll find a party atmosphere with DJs spinning during brunch and in the evenings, though you can also enjoy a more laid back vibe if you stop in for sushi and classic cocktails before catching a show in the Theater District.

  • Restaurants
  • Argentinian
  • Loop

Enjoy tropical vibes beneath a retractable glass roof on the 15th floor of the Kimpton Gray Hotel. Boleo serves South American-inspired dishes such as ceviche and anticuchos along with seasonal pisco cocktails. Come for happy hour from 5-6pm Tuesday through Saturday to take advantage of $8 ceviche and discounted beer and wine.

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  • Restaurants
  • Mediterranean
  • West Loop

Stay toasty on the partially covered rooftop patio by sitting around one of the fire pits or under a heater while sipping a glass of fortified wine or a cocktail like a spiced pear negroni. If you’re still feeling chilly, you can ask for a blanket and get really cozy between bites of smoky garlic hummus and grilled cauliflower kebabs.

  • Restaurants
  • Contemporary American
  • Loop
  • price 3 of 4

Look out over Lake Michigan and Millennium Park from the glass atrium on top of the Chicago Athletic Association hotel. The outdoor terrace is also accessible year round and features fire pits to keep you toasty while you sip an old fashioned. Cindy’s is running an autumn pop-up bar with themed decorations and cocktails on weekends through November 26.

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