7 Chicago Rooftop Bars to Visit This Summer

It’s the most wonderful time of the year: Rooftop season in Chicago! If Chicagoans love one thing, it’s al fresco dining and drinks with a view. When winter finally begins to fade away, patio furniture instantly appears on sidewalks, and hotels begin opening their rooftop bars for the season. And by season, we mean three months that slip away too soon. So, with the temperatures finally rising, be sure to grab a seat with a view at one of the most popular rooftop bars around the city.

Cindy’s

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Enter the main floor of the Chicago Athletic Association Hotel, and just opposite Shake Shack, you’ll find thirsty patrons standing in a line marked off with a red, velvet rope. You’re in the right place. Stand in line and you’ll be transported to the hotel’s famous rooftop bar, Cindy’s, where you’ll find the best views of Lake Michigan, the Bean, Millenium Park, and bustling Michigan Avenue below. The unbeatable views, coupled with their equal parts divine to look at and drink cocktails make waiting in said line worth it, we promise. If you’re looking for food, we highly recommend you make a reservation in advance to snag a coveted seat for brunch or dinner.

Tip: If the rooftop is slammed, the hotel is home to 4 other great watering holes like the Game Room, the Cherry Circle Room, and the Milk Room, a 12-seat speakeasy.

Ballast Point

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What happens when a San Diego based brewery opens a taproom in the midwest? You guessed it––a rooftop tasting room. Ballast Point brings you casual California vibes, over 40 different brews, and no-nonsense bar bites. If you get sick of the view (unlikely), go downstairs and take a tour of the brewery

The J. Parker

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Come for the rotating cocktail menu, order the burger, and then stay for the unobstructed views of Lake Michigan. Located on the 13th floor of Hotel Lincoln, the J. Parker sits perched over Lincoln Park. On any given weeknight we can guarantee a dimly lit spot perfect for dates, and on the weekends, you’ll find a DJ blasting crowd-pleasers while everyone drinks away the Sunday scaries. This all-occasion bar is nice enough to host a baby shower, and lowkey enough to dress down (read: yoga pants and tennis shoes).

Bernie’s

If you’re looking for a casual River North spot for happy hour, Bernie’s is a solid option with their breezy rooftop and Mediterranean inspired cuisine. While the views aren’t as dramatic as some of our other picks, you won’t be complaining with a $7 glass of wine in your hand. If happy hour turns into, well, not happy hour, they have a great dinner menu as well to keep the party going.

LH on 22

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Have out of town visitors? Take them to the rooftop at London House. With iconic views of the city, the Chicago River, and all of the bridges, the London House remains a favorite among tourists and locals alike. They have both an indoor lounge you can dine at and an outdoor terrace for snapping the perfect picture with the skyline as your backdrop.

Waydown

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The West Loop is home to the tastiest and trendiest food and bar scene in Chicago, so it’s no wonder Waydown calls it home. This bar and lounge spans the length of the 7th floor of the Ace Hotel and offers stunning views of the skyline, especially at sunset. Inside you’ll find an industrial setting paired with sleek furniture, surrounded by two outdoor patios. Stop by on the weekend for frozen cocktails and a live DJ, or come after work on Monday to enjoy their $6 menu.  

The Up Room

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The Robey, an art-deco office building turned stylish hotel, has quickly become a Wicker Park staple for boozy brunches and drinks with skyline views. This 13-floor hotel is the tallest building in the neighborhood, so the views of downtown Chicago are unobstructed and downright gorgeous. Space here is limited, so we recommend coming early, or popping up after brunch at Cafe Robey, located on the first floor.

Celeste

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This 4 AM bar has three different levels to dine and drink, but the roof garden is where it’s at. The bar is fully enclosed, but they bring the outdoors inside with ivy climbing up one wall and palm fronds lining another. The ornate seating options are reminiscent of tea time in a royal garden (yes really), but their sleek bar serves drinks a touch stronger.

For more things to do and see in Chicago, check out our city guides!