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8 Magical Chicago Rooftop Bars Offering Cozy Winter Hideouts

By Elliot McGowan

8 Magical Chicago Rooftop Bars Offering Cozy Winter Hideouts

Take it to the rooftops!

As winter grips hold of Chicago and the global pandemic forces restrictions on indoor dining some of the places we now find ourselves turning to are Chicago’s renowned rooftop bars and rooftop restaurants. Chicago’s rooftops offer thriving utopias in the summer months, but the frosty winters force many rooftops to retreat indoors and wait out the cold.

With retreating to the coziness of the indoors out of the equation this year a few rooftops have persevered to keep their spaces alive and kicking. Many have resorted to igloos, ski lodges, gingerbread houses, fire pits, and more, ensuring that a memorable night up among the Chicago skyline can still be had in the months to come.

We’ve put together a list of the most unique rooftops around Chicago that are still open through winter! From mouthwatering Mediterranean food in cute greenhouses to curling competitions with complimentary cocktails. Check out these awesome Chicago rooftop spots.

1. Joy District Chicago’s Rooftop

There are few rooftops that can compete with the astounding set up at Joy District’s Heated Winter Wonderland Rooftop And Holiday Cocktails. Sparkling lights, comfortable patterned couches, and impeccable views of Chicago’s skyline guarantee a memorable night but it’s the magic of vibrant murals and cascading greenery that truly makes Joy District’s rooftop a unique space.

Both Rooftop Ski Lodge and Rooftop Winter Igloos can now be rented ensuring a safe and private space to drink beneath the Chicago stars and skyscrapers with your chosen quarantine crew. You’ll have to be quick mind, as dates are quickly filling up.

You can find Joy District’s rooftop at 112 West Hubbard Street. 

2. The Gwen Hotel’s Rooftop

If you’re looking for something a little different, The Gwen Hotel’s rooftop has the answers. The luxury hotel has kitted its rooftop out with not igloos, not ice skating, but an outdoor curling rink high in the sky. 45-minute curling sessions are $30 per person and come with a complimentary round of cocktails meaning you can sip away on your favorite tipple while battling your buddies. Assemble your most accurate amigos and head to The Gwen Hotel rooftop for a memorable night of curling and cocktails.

You can find The Gwen Hotel’s rooftop at 521 North Rush Street.

3. London House Chicago’s Rooftop

On the 22nd floor of London House Chicago, a stunning rooftop overlooking the Chicago River and the hustle and bustle of Michigan Avenue can be found. This year the hotel launched its first-ever ‘Rudolph’s Rooftop’ experience and it looks absolutely magical. Whimsical décor, rentable outdoor igloos, and celebratory cocktails served from their iconic ice bar create a unique experience that shouldn’t be missed. Heaters and blankets mean you can enjoy the fantastic panoramic views while staying warm and cozy beneath the stars.

You can find London House’s rooftop at 85 East Wacker Drive.

4. The Godfrey Hotel Rooftop

The Godfrey Hotel is home to Chicago’s largest indoor-outdoor rooftop with a retractable roof that gives it the versatility to transform into any type of venue it desires. With the current health and safety restrictions in place, the roof will be retracted throughout winter offering fine dining and extraordinary views all season long. Heated igloos of various sizes have been erected for a winter wonderland that includes fire pits, fire dancing, live DJs, s’mores, and, of course, themed cocktails.

You can find The Godfrey Hotel’s rooftop at 127 West Huron and Lasalle.

5. Whiskey Business’s Rooftop Patio

On a 3000-square-foot Wicker Park rooftop high above 1367 N Milwaukee Avenue, Whiskey Business has created a multifunctional space that will be running events throughout winter. Rooftop movie nights, rentable gingerbread houses, weekend brunches, and MSU or Chicago Bears gameday packages offer something for everybody. On specific nights of December, Christmas classics will be shown on two 120-inch screens at the rooftop drinking haven turning it into a cozy cinema-viewing theater.

You can find Whiskey Business’s rooftop at 1367 North Milwaukee Avenue.

6. Aba’s Fulton Market Rooftop

Aba is a Mediterranean restaurant with a rooftop patio located in Chicago’s historic Fulton Market District. The low-key rooftop patio has now erected cute greenhouses so you can privately and safely enjoy dishes from all over the Mediterranean including Israel, Lebanon, Turkey, and Greece. Signature dishes include Crispy Short Rib Hummus, Jerusalem Bagel with Labneh, Char-Grilled Lamb Chops, and Skirt Steak Shawarma. Their bar menu also features rare Mediterranean-inspired wines, spirits, and cocktails to accompany a unique dinner within your own little glass rooftop house under the stars.

You can find Aba’s rooftop at 302 North Green Street.

7. The Woodlawn’s Rooftop

The Woodlawn’s exclusive rooftop has an igloo equipped with comfortable trendy decor making it the perfect place for a romantic evening or a night out with friends. It’s the contents of the evening on offer, however, that make it a top rooftop option. Each two-hour reservation includes a 3-course meal and alcoholic beverage selections but if bottle service doesn’t tickle your fancy, the Woodlawn has a bring your own booze policy. To make the night even more unique the igloo can be decked out in roses for $50 and, for bookings of 5 and less, a live musician can sweeten the rooftop experience for $100.

You can find Woodlawn’s rooftop at 1200 East 79th Street.

8. The Kennedy Rooftop

The Kennedy Rooftop is Wicker Park’s very own urban chic hideout. The interior, food, and drink options are all designed to accentuate the modern, trendy, and diverse fabric of Wicker Park. Panoramic views of Chicago’s iconic skyline and a comfortable layout make it a phenomenal rooftop option and luckily it’s set to stay open through winter. Like The Gwen Hotel, the Kennedy Rooftop is also home to a curling lane meaning you can enjoy a classy evening on the plush rooftop with a bit of competitive fun to keep you warm.

You can find The Kennedy rooftop at 1551 West North Avenue.

See more: 10 Gorgeous Wedding Venues In And Around Chicago