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Pilsen Yards patio
Photograph: Sammy Faze Photography

10 wonderfully cozy outdoor dining spots in Chicago

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

Morgan Olsen
Emma Krupp
Written by
Morgan Olsen
Contributor
Emma Krupp
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The temperature might be dropping, but that doesn't mean patio season has to end now that fall in Chicago has arrived. After last year's push for expanded patio dining options, some of the best outdoor restaurants in Chicago are now outfitted with heavy-duty heat lamps, firepits and even heated flooring to keep you toasty even as a chill starts to settle in the air. With a hot cocktail in hand and a rib-sticking meal on your plate, we bet you'll barely even notice the cold (if only for an evening). Grab your warmest sweater and make a reservation at one of the coziest outdoor dining spots in Chicago.

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Where to dine outdoors this fall

  • 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.

  • Restaurants
  • American
  • River West/West Town
  • price 2 of 4

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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  • 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, which includes a complimentary signature cocktail for everyone in your group. 

  • Restaurants
  • Contemporary American
  • River West/West Town
  • price 2 of 4

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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  • Bars
  • Hotel bars
  • Streeterville
  • price 3 of 4

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.

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

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.

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  • Restaurants
  • Mexican
  • Lower West Side

Pilsen Yards—the music-centric taco joint that opened in the former Monnie Burke's space earlier this year—has a sweet outdoor patio equipped with fireplaces, but you'll likely find the coziest vibes on the patio's enclosed section. Open year-round, the enclosed patio boasts radiant-heated cement flooring and overhead heaters, chic wood beams and a transluscent roof perfect for bringing in all of the outdoor light with none of the chill. 

  • Restaurants
  • Eclectic
  • Logan Square
  • price 2 of 4

Cozy vibes abound at this Alpine-inspired spot in Logan Square, which has modeled its rustic settings on the hiking lodges of Switzerland, France and southern Germany. If you want to take the Après-ski theme a step further, opt for dinner on the outside patio, where you'll find a roaring kettle firepit and liqueur-spike hot cocoa are just as warming as the hearty food in front of you. 

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  • Bars
  • Sports Bars
  • Logan Square
  • price 2 of 4

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.

  • Restaurants
  • Lake View

Seeing a show at Schubas any time soon? Grab dinner at the adjoining restaurant Tied House, where you can sidle up to a massive outdoor fireplace with belly-warming mains like eggplant rigatoni and delicata squash schnitzel. Pair your meal with seasonal cocktails like Autumn Sweater, which pairs vodka, apple cider, ginger, lemon and bubbly water for a spiced efect. 

 

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