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Photos by Lucy Hewett

Explore Like a Local: The Best Outdoor Drinking Spots in Chicago

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This advertising content was produced by Vox Creative without involvement from Vox Media editorial staff or Ballast Point.

Between jaunts to Lake Michigan, outdoor concerts, baseball games, and street festivals galore, nothing beats Chicago in the summertime. Realizing the effect warmer months have on city dwellers, Chicago’s top restaurants and bars are on the case, opening up their patios, backyards, and rooftops to win us over for starlit nightcaps and all-day revelry alike. From meticulously crafted cocktails at skyscraper heights to a brew on decidedly on-point patios, here are 10 of Chicago’s best spots for outdoor drinking this summer.

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Howells & Hood

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If it’s options you’re after, it’s all about the patio at this Mag Mile eatery that boasts one of the biggest outdoor bars in the city, complete with 300 seats and 120 beers on tap. Oversized umbrellas, infrared heating, and two granite-topped communal tables built for 16 are all the more reason to gather a crowd for happy hour and weekend celebrations — or for any summer season sports spectacles, which you can catch on all 29 of the venue’s 60-inch flat screens while sipping on a beer.

Lucy Hewett

Sweetwater Tavern & Grille

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When it comes to escaping the midday or after-hours hustle of the Mag Mile, this patio is it. More than 18 beers are on draft and just over 60 cans are on offer, meaning beer enthusiasts can have their pick when catching anything on the big screen (there are 24 of them here). Cocktail fans are in good hands, too — a medley of mules includes everything from a traditional riff to Dutch, London, Mayan, and Kentucky variations featuring orange vodka, gin, tequila, and bourbon, respectively.

Lucy Hewett

Bar Siena

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It might be Top Chef alum Fabio Viviani’s Italian fare that gets folks in the doors of this West Loop corner fixture, but once they’re in, it’s the 40-seat patio, extensive beer and wine list, and large format cocktails that help them stay put. Post-visit be sure to hit up BomboBar, the restaurant’s to-go window for from-scratch gelato, doughy bombolini, digestifs, and boozy Italian ice.

Lucy Hewett

Whiskey Business

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This second-floor rooftop is tucked away from street view and loaded with big screen TVs (including three 200-inch ones, to be exact) and oversized couches, making it an idyllic escape when every other bar is racked with lines and cover charges come game time. Be sure to catch the lemonade stand, a weekends-only amenity serving up Capri Sun pouch cocktails, boozy popsicles, and frozen spiked lemonade.

Lucy Hewett

Hopleaf Bar

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Guests can rest assured that they’re in store for something new with each visit to this Uptown happy hour haven, where more than 400 beers by the bottle and 68 drafts (which they rotate out five times a week) are on offer for patrons. The options only increase on the 48-seat patio, where the team has been known to grow hops for local home brewers, apples for cider that they press in-house, and herbs and produce for their Belgian-focused menus.

Lucy Hewett

Located on the 26th floor of the Dana Hotel, this River North newcomer has it all: stunning cityscape vistas, a grassy outdoor space plus fire pit, and show-stopping cocktails from the same team that brought us The Berkshire Room and The Sixth. Take, for example, the Nymph — a Collins glass of vodka, soda, and raspberry powder that’s topped off with an edible, elderflower-laced butterfly. If you’re looking for something a little less precious, it’s all about the Mr. Nice Guy, a “bong” of vodka, white sage, pineapple, and dehydrated blackberry that actually smokes when you sip it.

Cocktails undergo a Japanese-inspired makeover at this recently opened rooftop, where beverage director Michael Fawthrop mixes up spinoffs like the Sake Sangria (with sake, sparkling wine, watermelon, and eau de vie), the Toki Old Fashioned (with Japanese whiskey, honey, and bitters) and the Kyoto Collins (with green tea-infused gin, lemongrass lime, and soda). Take it all in amidst 21st floor skyline views, Japanese plates from chef Jordan Dominguez, and wow-factor design details like fire pit tables and dreamy string lighting.

Lucy Hewett

Homestead on the Roof

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It doesn’t get much fresher than this West Town destination, where a 3,500-square-foot organic rooftop garden supplies ample inspiration for the team’s food and drink menus — and for the Instagram posts of its al fresco diners. Sample their yield firsthand in drams like the Friction Meets Floral, with rye, grapefruit juice, and fermented habanero, or the Birds & the Bees, with gin, yellow chartreuse, and lavender honey.

Lucy Hewett

Big Star

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If ever there was a place to gather with friends for post-work rounds, stay into the wee hours for more of the same, and return the next day to do it all over again, Big Star would be it. Sure, the tacos strike the perfect balance of authentic and curiosity-piquing, and you get your money’s worth with the house margaritas (made with both tequila and mezcal here), but it’s the patio we credit for rounding up one of the city’s liveliest and most dedicated crowds of sun basking taco-tequila lovers. Order a beer and stay awhile — the party is just getting started.

Park & Field

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This self-coined vintage sports club may have opened doors in the height of winter, but make no mistake about it — it’s a summer destination through and through. That’s because a 6,000-square-foot patio makes room for everything and more you’d want in lazy, sunny days, from bocce ball leagues and frozen rosé to a Tuesday night movie series showcasing sports-inspired favorites like Field of Dreams, Major League, and Happy Gilmore. The outdoors only get better with a rotating draft list of a dozen brews, including a couple of special editions every Thursday night.

Lucy Hewett
This advertising content was produced by Vox Creative without involvement from Vox Media editorial staff or Ballast Point.

Howells & Hood

Lucy Hewett

If it’s options you’re after, it’s all about the patio at this Mag Mile eatery that boasts one of the biggest outdoor bars in the city, complete with 300 seats and 120 beers on tap. Oversized umbrellas, infrared heating, and two granite-topped communal tables built for 16 are all the more reason to gather a crowd for happy hour and weekend celebrations — or for any summer season sports spectacles, which you can catch on all 29 of the venue’s 60-inch flat screens while sipping on a beer.

Lucy Hewett

Sweetwater Tavern & Grille

Lucy Hewett

When it comes to escaping the midday or after-hours hustle of the Mag Mile, this patio is it. More than 18 beers are on draft and just over 60 cans are on offer, meaning beer enthusiasts can have their pick when catching anything on the big screen (there are 24 of them here). Cocktail fans are in good hands, too — a medley of mules includes everything from a traditional riff to Dutch, London, Mayan, and Kentucky variations featuring orange vodka, gin, tequila, and bourbon, respectively.

Lucy Hewett

Bar Siena

Lucy Hewett

It might be Top Chef alum Fabio Viviani’s Italian fare that gets folks in the doors of this West Loop corner fixture, but once they’re in, it’s the 40-seat patio, extensive beer and wine list, and large format cocktails that help them stay put. Post-visit be sure to hit up BomboBar, the restaurant’s to-go window for from-scratch gelato, doughy bombolini, digestifs, and boozy Italian ice.

Lucy Hewett

Whiskey Business

Lucy Hewett

This second-floor rooftop is tucked away from street view and loaded with big screen TVs (including three 200-inch ones, to be exact) and oversized couches, making it an idyllic escape when every other bar is racked with lines and cover charges come game time. Be sure to catch the lemonade stand, a weekends-only amenity serving up Capri Sun pouch cocktails, boozy popsicles, and frozen spiked lemonade.

Lucy Hewett

Hopleaf Bar

Lucy Hewett

Guests can rest assured that they’re in store for something new with each visit to this Uptown happy hour haven, where more than 400 beers by the bottle and 68 drafts (which they rotate out five times a week) are on offer for patrons. The options only increase on the 48-seat patio, where the team has been known to grow hops for local home brewers, apples for cider that they press in-house, and herbs and produce for their Belgian-focused menus.

Lucy Hewett

Apogee

Located on the 26th floor of the Dana Hotel, this River North newcomer has it all: stunning cityscape vistas, a grassy outdoor space plus fire pit, and show-stopping cocktails from the same team that brought us The Berkshire Room and The Sixth. Take, for example, the Nymph — a Collins glass of vodka, soda, and raspberry powder that’s topped off with an edible, elderflower-laced butterfly. If you’re looking for something a little less precious, it’s all about the Mr. Nice Guy, a “bong” of vodka, white sage, pineapple, and dehydrated blackberry that actually smokes when you sip it.

Noyane

Lucy Hewett

Cocktails undergo a Japanese-inspired makeover at this recently opened rooftop, where beverage director Michael Fawthrop mixes up spinoffs like the Sake Sangria (with sake, sparkling wine, watermelon, and eau de vie), the Toki Old Fashioned (with Japanese whiskey, honey, and bitters) and the Kyoto Collins (with green tea-infused gin, lemongrass lime, and soda). Take it all in amidst 21st floor skyline views, Japanese plates from chef Jordan Dominguez, and wow-factor design details like fire pit tables and dreamy string lighting.

Lucy Hewett

Homestead on the Roof

Lucy Hewett

It doesn’t get much fresher than this West Town destination, where a 3,500-square-foot organic rooftop garden supplies ample inspiration for the team’s food and drink menus — and for the Instagram posts of its al fresco diners. Sample their yield firsthand in drams like the Friction Meets Floral, with rye, grapefruit juice, and fermented habanero, or the Birds & the Bees, with gin, yellow chartreuse, and lavender honey.

Lucy Hewett

Big Star

If ever there was a place to gather with friends for post-work rounds, stay into the wee hours for more of the same, and return the next day to do it all over again, Big Star would be it. Sure, the tacos strike the perfect balance of authentic and curiosity-piquing, and you get your money’s worth with the house margaritas (made with both tequila and mezcal here), but it’s the patio we credit for rounding up one of the city’s liveliest and most dedicated crowds of sun basking taco-tequila lovers. Order a beer and stay awhile — the party is just getting started.

Park & Field

Lucy Hewett

This self-coined vintage sports club may have opened doors in the height of winter, but make no mistake about it — it’s a summer destination through and through. That’s because a 6,000-square-foot patio makes room for everything and more you’d want in lazy, sunny days, from bocce ball leagues and frozen rosé to a Tuesday night movie series showcasing sports-inspired favorites like Field of Dreams, Major League, and Happy Gilmore. The outdoors only get better with a rotating draft list of a dozen brews, including a couple of special editions every Thursday night.

Lucy Hewett

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