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An aerial view of rooftops with the Chicago skyline in the distance.
The view from Kennedy Rooftop on top of the Hyatt Place hotel in Wicker Park.
Barry Brecheisen/Eater Chicago

Where to Drink Outdoors in Bucktown, Wicker Park, and West Town

Rooftops, sidewalks, and plenty of dog-friendly patios

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The view from Kennedy Rooftop on top of the Hyatt Place hotel in Wicker Park.
| Barry Brecheisen/Eater Chicago

The trendy neighborhoods of Bucktown, Wicker Park, and West Town are known for their lively restaurants and bars. They get even busier during the summer when seasonal pop-ups open and year-round spots set up their patios or open up retractable roofs to let in the fresh air and sunshine. From a dog-friendly brewery to a chic rooftop with bottle service, here are 10 spots to enjoy the weather and a delicious drink.

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Note: Restaurants on this map are listed geographically.

Cabana Club

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The seasonal rooftop bar on the sixth floor of the Robey hotel offers views of the Chicago skyline and the rooftops of Wicker Park and Bucktown’s many churches. Lounge under an umbrella by the pool and try something from the new menu of piña coladas and frozen margaritas in flavors including prickly pear and peach ginger.

Kennedy Rooftop

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Take in skyline views from the top of the Hyatt Place Wicker Park, which features lounge seating, fire tables, and giant Jenga sets. Swing by for a White House-themed cocktail like the Jackie-O (rhubarb gin, champagne, and lemon) or go all out by booking a cabana with mimosa or margarita bottle service plus a meat and cheese platter.

There’s space for groups of all sizes on the back porch of Cebu, where there are both umbrellas and heaters to provide shade on sunny days and keep drinkers warm on cool evenings.. Take advantage of 90 minutes of bottomless mimosas for $25 during brunch along with the equally decadent ube chicken waffle sandwich served with black truffle tamarind seasoned fries.

Big Star

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Wicker Park honky tonk Big Star boasts one of the most sought-after patios in the city, a huge sunny, dog-friendly space shaded by bright yellow umbrellas and surrounded by planters. On a nice day, expect to find it packed with groups sharing pitchers of palomas or margaritas, whiskey cocktails, and family-style platters of tacos wrapped in handmade corn tortillas.

The Perch Kitchen and Tap

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There’s plenty of room to enjoy the weather in the Perch’s ivy-covered beer garden or on the dog-friendly patio, where your best friend can enjoy a pupsicle or puppy power protein bowl. Get a taste of the brewery’s novel beers like Inari Japanese-style lager brewed with jasmine rice and Queen of Funk kiwi kettle sour ale, or sip an equally refreshing cocktail like the Atticus (Koval cranberry gin, bergamot, lime, hibiscus syrup, and housemade seltzer).

Easy Bar

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Drink on the cheap on the dog-friendly sidewalk patio at Easy Bar, where everything is half price from 5 p.m. to 7 p.m. Monday through Thursday and 4 p.m. to 6 p.m. Friday through Sunday. There’s room for 15 to 20 people to sit at tables surrounded by planters: it’s a laid-back space to sip an Aperol spritz or the super strong Easy Punch #7, a draft cocktail made with vodka, gin, pineapple, and lemon.

Mama Delia

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Mama Delia sets up a seasonal pavilion on the sidewalk that gives diners a choice of tables protected from the rain or in the open air under strings of lights. Ferns hang overhead and pink wine barrels serve as planters, providing a lush space to sip a Spanish-style gin & tonic or something from the Wicker Park restaurant’s extensive sherry list.

Frontier

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Frontier’s rustic lodge vibe extends to its beer garden, which is decorated with piles of chopped wood, potted cacti, and cushioned Adirondack chairs, though it still offers the modern conveniences of TVs and ceiling fans. Visit Wednesdays for $5 glasses of wine paired with raw or char-grilled oysters or gather a group any day to share a pitcher of chipotle or pineapple-jalapeno margaritas. 

Beatnik West Town

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Beatnik’s opulent garden and courtyard feature a retractable roof, and awnings that shade the couches along the walls. Best of all, there’s plenty of room for diners under the chandeliers. Come Tuesday evenings to catch a live percussion set while sipping out of a chilled young coconut filled with rum, pineapple, lime, and ginger, or sharing a group cocktail like the Got Stones, a blend of tequila, aperol, grapefruit, orange, and pomegranate.

District Brew Yards

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Decorated with bright-colored murals, the dog-friendly patio at the pour-your-own beer hall District Brew Yards offers plenty of space to try some of the 40 beers on tap from Around the Bend Beer Co., Burnt City Brewing, Bold Dog Beer Co., and Casa Humilde Cervecería. There’s also food from Lillie’s Q and Chicken Shack. Large groups looking to secure space can book a cabana. 

Cabana Club

The seasonal rooftop bar on the sixth floor of the Robey hotel offers views of the Chicago skyline and the rooftops of Wicker Park and Bucktown’s many churches. Lounge under an umbrella by the pool and try something from the new menu of piña coladas and frozen margaritas in flavors including prickly pear and peach ginger.

Kennedy Rooftop

Take in skyline views from the top of the Hyatt Place Wicker Park, which features lounge seating, fire tables, and giant Jenga sets. Swing by for a White House-themed cocktail like the Jackie-O (rhubarb gin, champagne, and lemon) or go all out by booking a cabana with mimosa or margarita bottle service plus a meat and cheese platter.

Cebu

There’s space for groups of all sizes on the back porch of Cebu, where there are both umbrellas and heaters to provide shade on sunny days and keep drinkers warm on cool evenings.. Take advantage of 90 minutes of bottomless mimosas for $25 during brunch along with the equally decadent ube chicken waffle sandwich served with black truffle tamarind seasoned fries.

Big Star

Wicker Park honky tonk Big Star boasts one of the most sought-after patios in the city, a huge sunny, dog-friendly space shaded by bright yellow umbrellas and surrounded by planters. On a nice day, expect to find it packed with groups sharing pitchers of palomas or margaritas, whiskey cocktails, and family-style platters of tacos wrapped in handmade corn tortillas.

The Perch Kitchen and Tap

There’s plenty of room to enjoy the weather in the Perch’s ivy-covered beer garden or on the dog-friendly patio, where your best friend can enjoy a pupsicle or puppy power protein bowl. Get a taste of the brewery’s novel beers like Inari Japanese-style lager brewed with jasmine rice and Queen of Funk kiwi kettle sour ale, or sip an equally refreshing cocktail like the Atticus (Koval cranberry gin, bergamot, lime, hibiscus syrup, and housemade seltzer).

Easy Bar

Drink on the cheap on the dog-friendly sidewalk patio at Easy Bar, where everything is half price from 5 p.m. to 7 p.m. Monday through Thursday and 4 p.m. to 6 p.m. Friday through Sunday. There’s room for 15 to 20 people to sit at tables surrounded by planters: it’s a laid-back space to sip an Aperol spritz or the super strong Easy Punch #7, a draft cocktail made with vodka, gin, pineapple, and lemon.

Mama Delia

Mama Delia sets up a seasonal pavilion on the sidewalk that gives diners a choice of tables protected from the rain or in the open air under strings of lights. Ferns hang overhead and pink wine barrels serve as planters, providing a lush space to sip a Spanish-style gin & tonic or something from the Wicker Park restaurant’s extensive sherry list.

Frontier

Frontier’s rustic lodge vibe extends to its beer garden, which is decorated with piles of chopped wood, potted cacti, and cushioned Adirondack chairs, though it still offers the modern conveniences of TVs and ceiling fans. Visit Wednesdays for $5 glasses of wine paired with raw or char-grilled oysters or gather a group any day to share a pitcher of chipotle or pineapple-jalapeno margaritas. 

Beatnik West Town

Beatnik’s opulent garden and courtyard feature a retractable roof, and awnings that shade the couches along the walls. Best of all, there’s plenty of room for diners under the chandeliers. Come Tuesday evenings to catch a live percussion set while sipping out of a chilled young coconut filled with rum, pineapple, lime, and ginger, or sharing a group cocktail like the Got Stones, a blend of tequila, aperol, grapefruit, orange, and pomegranate.

District Brew Yards

Decorated with bright-colored murals, the dog-friendly patio at the pour-your-own beer hall District Brew Yards offers plenty of space to try some of the 40 beers on tap from Around the Bend Beer Co., Burnt City Brewing, Bold Dog Beer Co., and Casa Humilde Cervecería. There’s also food from Lillie’s Q and Chicken Shack. Large groups looking to secure space can book a cabana. 

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