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Upstairs at the Gwen
Photograph: Courtesy The Gwen Upstairs at the Gwen

11 wonderfully cozy outdoor dining spots in Chicago

These restaurants are stretching the alfresco season in new and unique ways

By Morgan Olsen
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In classic Chicago fashion, it feels like the temperature is steadily dropping every single day. Meanwhile, city officials are still encouraging restaurants to extend outdoor dining for as long as humanly possible, resulting in tents, igloos and heaters being set up all over town. If you're willing to brave the cold, there are plenty of super cozy patios and rooftop restaurants in Chicago to check out this season. Dust off your favorite coat and make a reservation at one of these outdoor dining spots this fall, which range ritzy rooftop lounges and a sprawling igloo village to a festive pumpkin patch for families. It goes without saying, but if you are dining out this fall, mask up, mind your social distancing manners and tip your servers generously.

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Where to dine outdoors this fall

Photograph: Heidi Harris – Our Labor of Love

VU Rooftop Bar

Bars Near South Side

Perched 22 stories above street level, VU stays true to its name, with city vistas as far as the eye can see. The South Loop rooftop bar has 13,000 square feet of indoor and outdoor space, making it easy to carve out your own space. The most coveted seats in the house surround a stone fire pit on the terrace—from here, you can post up and enjoy small plates, sandwiches and large-format cocktails.

The Dawson
Photograph: Martha Williams

The Dawson

Restaurants American River West/West Town

When the wind is howling, the six-corner intersection at Halsted Street and Grand Avenue can feel like a frozen tundra. Best to tuck inside the Dawson and grab a seat on the walled-off patio that's anchored by a massive, wood-burning hearth. It's also advisable to wait out the weather with a glass of brandy-spiked Autumn Sangria and an extra-large order of fries.

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Upstairs at the Gwen
Photograph: Courtesy The Gwen

Upstairs at The Gwen

Restaurants American River North

Dotted with towering heat lamps and modern fire pits, the sprawling patio at the Gwen always feels cozy, no matter the forecast. Guests can reserve tables or private loungey areas equipped with couches, but if you really want to do something unique, book the rooftop curling court for $30 per person, which includes a complimentary signature cocktail for everyone in your group. Just keep you group to six people or fewer and remember that your reservation is capped at 45 minutes.

frontier, brian jupiter
Photograph: Meghan Leigh Photography

Frontier

Restaurants Contemporary American River West/West Town

There are plenty of reasons to love Brian Jupiter's West Town restaurant, which specializes in carnivorous delights like char-grilled oysters and gargantuan wagyu ribs slicked in Carolina barbecue sauce. High on the list of perks is the covered patio, which offers alfresco dining well into the cold months. Strewn in twinkling lights and equipped with a roaring fireplace, there are few better places to while away an autumn afternoon.

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Z Bar cocktail
Photograph: Jess Paro

Z Bar

Bars Hotel bars Streeterville

The Peninsula's stunning rooftop lounge has it all: sweeping city views, classic cocktails, a roster of shareable snacks and chic fire pits to keep you warm. Cozy up on the couches and order a round of bourbon Old Fashioneds to cap off the evening. If the temperature drops, the beautifully appointed bar inside is an idyllic place to heat up before you head out.

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J Parker
Photograph: Ally Straussner

The J. Parker

Bars Lounges Lincoln Park

When the weather takes a turn for the chilly, this Lincoln Park rooftop bar closes its retractable roof and cranks up the heat, creating a snowglobe effect for diners inside—minus the snow, of course. Every seat in the house boasts stellar views featuring the twinkling skyline, Lincoln Park Zoo and the vast expanse that is Lake Michigan. Pad your belly with a stacked burger before tucking into seasonal cocktail creations.

Hocus Pocus pop-up bar
Photograph: Homestead On The Roof/Sarah Zelman

Homestead On The Roof

Restaurants Contemporary American East Village

This fan-favorite rooftop restaurant in West Town is being transformed into a Hocus Pocus-themed pop-up bar through November 8. The patio and heated interior are decked out in large-scale décor, including a glowing moon, zombies, tombstones and more clever nods to the 1993 family comedy. Rounding out the experience is a menu of themed cocktails and food, like the Amok! cognac sipper and the Devil Himself fried chicken sandwich.

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Daisies pumpkin patio
Photograph: Courtesy Daisies

Daisies

Restaurants Logan Square

Get your fall fun fix and a great meal without leaving town when you drop by Daisies's pumpkin patch, which is set up on the restaurant's back patio. The outdoor area has several tables that are generously spaced out to allow for social distancing while you dine. At lunchtime, the Logan Square kitchen serves stacked sandwiches and cold salads to go, but when the sun goes down, it's all about the delectable house-made pastas.

Dining Together, Apart
Photograph: Kevin Conway, Flightless Bird Creative

Dining Together, Apart

With city officials encouraging restaurants and bars to stretch outdoor dining setups into the winter months, a village of igloos and greenhouses has cropped up in the West Loop. It's a partnership between West Central Association, the Illinois Restaurant Association and Stella Artois to offer an outdoor seating solution for Fulton Market favorites Beatrix, the Publican, Kuma's Corner, Duck Duck Goat and Gus's World Famous Fried Chicken.

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Park & Field
Photograph: Courtesy Park & Field

Park & Field

Bars Sports Bars Logan Square

Though its kitchen and bar is housed in a former auto repair garage, Park & Field's main draw is its gigantic patio, which features a bocce court, fire pits and a camper that has been retrofitted to serve as an outdoor bar. Plan your visit for the weekend, when Park & Field hosts a bottomless boozy brunch with a "virtual" buffet (servers load up your plate just how you like it and deliver it straight to your table), priced at $45 per person.

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