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offshore, rooftop
Photograph: Courtesy Offshore

The 14 best rooftop bars in Chicago

Lounge around in the sun with a drink in your hand at one of the best rooftop bars in Chicago

By Morgan Olsen
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If there's one thing Chicagoans love more than drinking in the sun, it's drinking in the sun high above the city streets. This year, some of the best Chicago bars and restaurants are reopening their rooftops to vitamin D-deprived residents, who can expect new safety measures, capacity restrictions and masked servers. We'll do our best to keep this list updated as bars emerge from lockdown, but it's always wise to call ahead or check your favorite spot's social media accounts for pertinent updates.

These Chicago rooftop bars are officially open for the season, and there's no shortage of rosé, frozen cocktails and craft beer to go around. From posh lounges and sprawling terraces to quiet places to relax, the city's best rooftops come in all shapes and sizes. Scope out the best rooftop bars in Chicago and plan your summer imbibing accordingly.

Best rooftop bars in Chicago

Cindy's
Photograph: Thomas Hart Shelby

1. Cindy's

Restaurants Contemporary American Loop

When friends ask us where to take cocktail-loving out-of-towners, one spot always leads the pack: Cindy's. The rooftop restaurant and bar at the Chicago Athletic Association Hotel offers unparalleled views of the city, with an expansive look at Millennium Park and the Lake. But the real draw is a roster of excellent cocktails—like the Jillian with vodka, vermouth, spiced clementine and fresh lemon—and clever spirit-free elixirs.

Photograph: Jaclyn Rivas

2. Boleo

Restaurants Argentinian Loop

Even in the dead of winter, this beautiful rooftop bar at the Kimpton Gray Hotel feels like a tropical paradise. The menu here highlights South American flavors in drinks like the In the Morning, I'll Be Better, an addictive blend of plantain-infused Scotch, black walnut bitters, tiki bitters and smoke. Pair it with an order of the fan-favorite empanadas, which are stuffed with flank steak, red pepper and olives and served with chimichurri sauce.

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JParker1.OutdoorBars.jpg
Photograph: Martha Williams

3. The J. Parker

Bars Lounges Lincoln Park

If you haven't crossed the J. Parker off your Chicago bucket list, grab a glass of sparkling rosé and get to work. With its mesmerizing views of the city and Lincoln Park, this year-round rooftop bar is a must for entertaining out-of-towners. On particularly beautiful summer days, arrive early and be prepared to wait for a seat to open. It's worth it, promise!

bottom lounge, rooftop
Photograph: Courtesy Bottom Lounge

4. Bottom Lounge

Bars Lounges West Loop

You can't catch a concert at this West Loop music venue just yet, but the rooftop bar has reopened for alfresco dining and imbibing. Enter through the parking lot and follow the signs up the rear stairs—beers, booze and burgers await when the weather allows.

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offshore, rooftop
Photograph: Courtesy Offshore

5. Offshore

Bars Cocktail bars Streeterville

With 36,000 square feet of indoor and outdoor space to roam with a cocktail in your hand, Navy Pier's Offshore is the largest rooftop bar in the world. (Really.) The all-seasons venue includes a glass-enclosed bar where you can order a cocktail and some oysters, as well as an expansive outdoor terrace outfitted with fire pits and a stage for live performances.

Upstairs at the Gwen
Photograph: Courtesy The Gwen

6. Upstairs at the Gwen

Restaurants American River North

Situated on the fifth floor of the Gwen in River North, this posh 3,000-square-foot rooftop offers a unique view of the city, surrounding its guests with some of the city's coolest architectural gems. Expect signature cocktails and large-format drinks like the summer sangria pitcher.

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LH Rooftop at LondonHouse Hotel
Photograph: Nicholas James

7. LH Rooftop

Restaurants Loop

In a city full of sweeping views, everyone wants to be on top. But this tri-level venue is the tippy top of all rooftop bars. Located on the 21st floor of LondonHouse Chicago, LH Rooftop affords guests stunning vistas of the architecture along the Chicago River and Michigan Avenue. The only downsides: You'll have to arrive early if you want to find a seat, and the drinks aren't cheap. We recommend staying for a glass of bubbly, enjoying the view and moving on.

Photograph: Heidi Harris – Our Labor of Love

8. VU Rooftop Bar

Bars Near South Side

True to its name, the views at VU are epic from 22 stories above street level. Once you've secured a seat, order from a selection of classic cocktails (like the gin-based Last Word or the refreshing cherry mule) before ordering a few bites for the table. With three bars and two patios spread across 13,000 square feet, there's plenty of room to spread out and relax in the sun.

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fountainhead chicago
Photograph: Courtesy Fountainhead

9. Fountainhead

Bars Beer bars Lincoln Square

If you're looking to sip craft beer, bourbon or whiskey in the sun, you've come to the right place. When the weather permits, this North Center bar opens its rooftop garden to thirsty Chicagoans, pouring suds and ciders from local, national and international brewers like Whiner Beer Co., Ska Brewing and Brasserie de Silly. For something stronger, choose from a laundry list of bourbons, available as shots, drinks or as a Manhattan.

etta, jaclyn rivas, wicker park, food, restaurant
Photograph: Jaclyn Rivas

10. etta

Restaurants Wicker Park

Hit up this sweet Wicker Park rooftop for weekend brunch service, when you can enjoy tableside Aperol spritz service until you need to reapply your sunscreen. On your way out, grab something to go from the grill out front—the pic picnic pita is the perfect afternoon snack.

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I|O Godfrey rooftop
Photograph: Kailley Lindman

11. I|O at the Godfrey Hotel

Bars Lounges River North

There's not a bad seat in the house at this sprawling rooftop bar, which affords everyone a front-row seat to a postcard-worthy skyline view. Take in the vistas while sipping a CBD-infused cocktail, a glass of wine or a selection from the impressive mocktail menu. As the sun sets, refuel with wagyu beef sliders, spicy tuna rolls and chocolate lava cake.

Aba, rooftop, patio, outdoor dining, outdoor, restaurant
Photograph: Jeff Marini

12. Aba

Restaurants Mediterranean West Loop

The loungey, greenery-lined setup at this West Loop restaurant makes it easy to relax. The summer-ready cocktails don't hurt either—including Day One favorite Aloe? It's Me with mezcal, aloe, green juice, lime and jalapeño. Break for refreshing bites, like the spicy hummus, whipped feta dip or the big eye tuna carpaccio.

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whiskey business, rooftop
Photograph: Courtesy Whiskey Business

13. Whiskey Business

Bars Pubs Wicker Park

Opening at 9pm Thursday through Sunday, this Wicker Park rooftop offers a boozy respite tucked just above Milwaukee Avenue. Order from a menu of party-ready drinks like the Red Bull Tropical Tequila or a Miami Vice, then lean back and watch the lights show, which is set to tunes from the '80s and '90s, with some top-40s hits sprinkled in.

Photograph: Courtesy Joy District

14. Joy District

Restaurants Contemporary American River North

There's no getting around it: Joy District is a scene. The perfectly manicured rooftop terrace is buzzing with bottle service, glasses of frosé and buckets of White Claw. If you're looking for something a bit more low-key, show up for brunch early on the weekends; and if you're hoping to turn up, you'll find what you're looking for anytime after 5pm.

Find more of the best rooftops in Chicago

Homestead is one of the best rooftop restaurants in Chicago.
Photo: Jason Little

The best rooftop restaurants in Chicago

Restaurants

The best rooftop restaurants offer both great food and city views, whether you're gazing at views of the Chicago Loop or glimpses at neighborhood architecture. From one of the best Italian restaurants in the city to a spot for brunch in Chicago, here's where to head this summer.

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