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Chicago's best outdoor drinking secrets

Uncover the city's best outdoor drinking spots, amazing cocktails, secret menu items and more

Photograph: Courtesy Cerise

Say what you will about Chicago's harsh winters—when the mercury begins to rise, nearly everyone in this city streams outside. We all have a favorite park, a preferred music festival and—most importantly—a patio or rooftop where we go to sip a drink in the sun. We've teamed up with Bulleit to uncover the secrets behind some of Chicago's best outdoor cocktail destinations.

RECOMMENDED: Explore more of Chicago's whiskey secrets

Chicago's outdoor drinking secrets

1

Parlor Pizza Bar

You can’t miss the patio at this West Loop pizza joint—it dominates the front of the restaurant, as unmistakable as the glowing neon sign that beckons hungry visitors. A rooftop bar makes this a choice destination for a few slices and a drink at the end of a long day.
Tip: Parlor may be known for its pizza, but the Craziest Bread is the secret star of the menu. Stuffed with garlic, mozzarella, cherry peppers and pepperoni, you’ll need some help finishing just one serving of this gooey beer bread.

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2

Belly Up Smokehouse & Saloon

You’ll find meat smoking at Belly Up year-round, but in the summer, the garage door on the front of the restaurant goes up and a makeshift patio allows guests to lick ribs in plain sight. Sit down at the bar, order a beverage and eat some candied bacon while admiring the Southern décor.
Tip: Located just blocks away from Museum Campus, a meal at Belly Up is the perfect way to start off an afternoon spent exploring artifacts at the Field Museum or watching fish swim at the Shedd Aquarium.

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Loop
3

Whiskey Business

We don’t suggest dancing into this Wicker Park bar without a pair of pants on, but you’re free to show up in a sharp pair of shades. Whiskey Business boasts a formidable list of bourbon, rye and scotch, as well as a rooftop patio where you can order ’80s-themed cocktail and toast the unbridled nostalgia on display.
Tip: Some bars put topping on their burgers, but Whiskey Business puts them inside the patty. You can try a burger stuffed with pork, crab cakes or mac and cheese—is that decadent enough for you? 

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Wicker Park
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4

Streeterville Social at the Loews Hotel

More of a gigantic playground than a simple rooftop lounge, Streeterville Social features a patch of grass where guests can play bags or topple an oversized Jenga set. Not looking for fun and games? The rooftop’s bar features a street food-inspired menu and creative cocktails.
Tip: No rooftop offers a better view of the Navy Pier fireworks display than this one. Arrive early on a Wednesday or Saturday night during the summer and prepare for an explosive evening.

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5

The Terrace at Trump

Jutting out from the 16th floor of the Trump Tower, the Terrace offers unparralelled views of the nearby Wrigley Building, Tribune Tower and Chicago River. There’s also an extensive menu to enjoy while you’re taking in the sights, including seafood platters, top-shelf cocktails and decadent desserts.
Tip: Looking for a drink with a unique flavor? Try the Smoking Man, made with bourbon, Maraschino liqueur and Amaro, before being infused with wild cherry bark smoke.

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River North
6

Chop Shop

This Wicker Park restaurant, bar and event space has it all—multiple bars, a killer cocktail menu, plenty of delicious meat and one of the only rooftop patios in the entire neighborhood. Take a seat, order a steak and relax in the in sun at this hideaway just above the bustling streets.
Tip: Love the steak or chops you ordered for dinner? Visit the butcher at the front of the shop after your meal and you can buy a few cuts to cook at home.

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Wicker Park
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7

Fatpour Tap Works

The stretch of Division Street that boarders Wicker Park is crawling with sidewalk patios, but you’ll be hard-pressed to find a bar with the sheer amount of that Fat Pour houses. With 50 beer taps, a cocktail menu and plenty of tasty grub, you’ll want to post up on an outdoor bench for hours on end.
Tip: See all those Badgers banners? This is a Wisconsin bar, so you need to order the fried cheese curds—trust us, you won’t be disappointed.

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Ukrainian Village
8

Derby

Named after the famous Kentucky horse race, this Southern bar and grill resides in a building with that housed a post-prohibition bar in the 1920s. Head straight for Derby’s ivy-covered patio and order a Hot Brown (an open-faced turkey, ham and bacon sandwich) and an expertly-crafted cocktail.
Tip: No matter the season, there’s no better way to get in the Derby spirit than with a crisp, refreshing mint julep.

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9
The Southern

The Southern

If dishes like frog legs, collard greens and hot fried chicken bring back fond memories, you’ll find all the comfort food you can handle at the Southern. Order a mint julep, snag a table on the outdoor patio and prepare to be transported down the Mississippi at this Wicker Park bar.
Tip: Looking for one of the best happy hour deals in town? Show up between 5-7pm on weekdays to enjoy $2 whiskey shots.

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10

Hopsmith Tavern

There’s almost always a game on at this Gold Coast bar, which bills itself as a destination for Michigan State supporters. If the cheers get too loud, you can escape to the second floor, where a retractable roof turns the room into a patio and beer is tapped from a 1954 Volkswagen Beetle station wagon.
Tip: Make yourself feel like a champ by ordering the Lord Stanley’s Sampler, which serves up a variety of appetizers in a replica Stanley Cup.

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11

The Scout

Frequented by local athletes and sports fans alike, this South Loop bar and restaurant is a destination for anyone who likes to watch a game among an enthusiastic crowd. On sunny days, the sidewalk patio is usually crammed with locals eating tater tots and nursing cocktails.
Tip: Need something to wash down that foot long grilled cheese sandwich? A Gramercy Manhattan should do the trick.

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12

The Hampton Social

Step into the Hampton Social and you’ll instantly be transported to the East Coast, where lobster rolls and oysters are plentiful and walls are typically adorned with oars or thick rope. The nautical theme extends to the cocktail menu, which features some tiki-inspired concoctions.
Tip: One section of the restaurant’s patio features hammock seating—the perfect way to relax while you sip on your cocktail.

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13

Sidetrack

Since opening in 1982, Sidetrack has become a Boystown institution, known for its frozen drinks and upbeat playlists. The walls are lined with TVs (this is a video bar, after all) but you can escape the clamor on the rooftop patio, which is covered in greenery and sports a miniature bar.
Tip: Fans of show tunes should stop by for Musical Mondays, when VJ Jose Pena leads spirited sing-alongs to hit Broadway songs from shows like Rent and Oklahoma.

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14

Happy Village

A night spent in the garden patio at Happy Village feels like a block party in your neighbor’s backyard. Draped in strings of lights and filled with tables and chairs, there’s plenty of space to strike up a conversation while you enjoy drinks and fresh air.
Tip: There's a two drink minimum if you want to use the bar’s ping pong tables, so order an extra drink on your way in if you don't want to interrupt your game.

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15

Cerise at Virgin Hotels Chicago

You’ll witness some breathtaking views atop the Virgin Hotel, so it’s no surprise that the menu, service and ambiance at the Cerise rooftop bar are equally impressive. Regular DJ sets mean that you can listen to tunes while you drink or get up and show off your skills on the dance floor.
Tip: Take a short walk downstairs to the 25th floor and you may find a free concert or movie screening taking place in a small bar located just below Cerise.

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16

iO Theater

When the iO Theater—which boasts famous alumni such as Mike Myers and Tina Fey—moved to its new Lincoln Park location, it gained a giant outdoor patio. On warm days, you’ll find performers and comedy-lovers sipping drinks and engaging in some witty banter between shows.
Tip: If you’ve never seen a show at iO, catch a weekly performance by the Improvised Shakespeare Company, in which a group of performers make up an Elizabethan play on the spot.

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17

Flo & Santos

The pizza and pierogi at this South Loop tavern are local favorites, best enjoyed with a refreshing cocktail and some good friends on hand. The adjacent patio is almost always packed on warm summer nights, as guests gobble up delectable Italian food and Polish delicacies.
Tip: Skip the delivery pizza and watch the game at Flo & Santos, where a 90-inch HD projector and eight flat screens broadcast all the biggest matches.

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18

Fountainhead

Known for its robust beer selection and extensive whiskey list, this Ravenswood gastropub is outfitted with a spacious rooftop that is usually packed with people. Show up early to snag a seat and make sure to ask your server for a few drink suggestions if you’re up for something different.
Tip: Visit the nearby Fountainhead Market (1966 W Montrose) to take purchase a bottle of whiskey to restock your home bar.

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Lincoln Square
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19

Bernie's Lunch & Supper

Named for its owner’s grandfather, Bernie’s brings a sophisticated supper club atmosphere to River North, offering a seasonal menu and a rotating selection of cocktails. Dress to impress and take a seat on the elegant rooftop patio—an ideal spot for a tranquil dinner or a rejuvenating brunch.
Tip: Expect a combination of disparate cuisines when dining at Bernie’s—for example, the pork confit supplements a Mediterranean dish with Korean kimchi pickles.

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River North
20

Maria’s Packaged Goods & Community Bar

As much as Bridgeport resident (and visitors) love to gather in Maria’s dimly lit bar, the community bar is even more popular during the summer months, when crowds spill out onto the patio. The outdoor space has plenty of benches where you can cool off with a cocktail made with locally sourced ingredients.
Tip: Don’t drink on an empty stomach! Order Polish and Korean-inspired cuisine from the nearby Kimski while you enjoy a drink on Maria's patio.

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Bridgeport
21

Cindy's

If you’ve seen an idyllic aerial shot of Grant Park pop up on your Instagram feed recently, there’s a good chance it was taken on the outdoor terrace at Cindy’s. The Chicago Athletic Association rooftop is perfect for small groups, with plates for sharing and cocktails that can be served in small and large formats.
Tip: Cindy’s isn’t just for dinner anymore—the rooftop space’s recently launched lunch service features a menu of sandwiches and sides for individual diners. Show up Monday through Friday between 11am and 2:30pm for a meal with a view. 

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Loop
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22

Maple & Ash

It’s difficult to have a drink at Maple & Ash without being tempted by the smell of wood-grilled steaks being delivered to tables throughout the upscale Gold Coast restaurant. Sitting outside on the newly opened patio may be a temporary solution, but after a few cocktails that giant porterhouse will only look more delicious.
Tip: While the downstairs bar focuses on martinis, the second floor offers up a selection of cocktails with names that reference classic movies.

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Rush & Division
23

Park Grill

Situated within spitting distance of Chicago attractions such as the Bean and Pritzker Pavilion, the Park Grill is the place to go if you want to eat and drink in the heart of the city. A menu of burgers, barbecue and simple cocktails makes this outdoor space a great place to cap off a day of summer fun.
Tip: Even if there’s nothing scheduled on the nearby stage in Millennium Park, you might be able to catch some free live music on the Park Grill patio—just check the schedule.

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Millennium Park
24

Luxbar

Run by the same team behind Gibsons Steakhouse, this Gold Coast lounge refers to itself as “the quintessential American bar,” serving up burgers, steaks and classic beverages. The street side patio is a departure from the wood-paneled ambiance of the interior, but the service is just as attentive.
Tip: If you’re the kind of person who knows exactly what they want, LuxBar’s build your own Manhattan menu serves up cocktails customized to your exact specifications. 

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Gold Coast
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