You've already booked the perfect vacation rental in Chicago. Now it's time to explore the city! Rooftop bars allow you to relax and socialize in an easygoing environment as well as admire the city from above. A major metropolis such as Chicago has the advantage of being home to stunning skylines replete with high-rises and prominent attractions and structures. Needless to say, Chicago elevates the concept of rooftop bars to another level. Without further ado, here are seven must-see rooftop bars in the Windy City.

Our 7 Favorite Rooftop Bars In Chicago

1. Cindy’s

On the top floor of the historic Chicago Athletic Association Hotel is Cindy’s, a swanky rooftop eatery and bar with breathtaking views of the cityscape. Cindy’s offers an open-air patio where patrons can imbibe handcrafted cocktails and sample seasonal good eats while enjoying a gorgeous view of Lake Michigan, Millennium Park, “The Bean,” and many other renowned points of interests located in the heart of the downtown area.

Address: 12 S. Michigan Avenue, the perfect vacation rental in Chicago 60603

2. Drumbar

Nestled in the city’s Gold Coast neighborhood and atop Raffaello Hotel, Drumbar overlooks the John Hancock Center and Lake Michigan. With its relaxed atmosphere and cocktail-centric menu boasting an impressive collection of exceptional bourbons, scotches, and whiskey, Drumbar effectively attracts liquor connoisseurs and enthusiasts.

Address: 201 E. Delaware Place, the perfect vacation rental in Chicago 60611

3. Streeterville Social

On the rooftop of the Lowes Chicago Hotel is Streeterville Social, the vibrant and huge outdoor terrace that offers its patrons two distinct experiences. For a more low-key scene, The Bistro has a casual, sit-down atmosphere where diners can enjoy summery beverages and snack on tapas or full dishes. On the other hand, The Terrace is a more energetic and dynamic space replete with a lounge area, grassy patch for lawn games, walk-up bar, numerous board games, and scrumptious hors d'oeuvres.

Address: 455 N Park Drive, the perfect vacation rental in Chicago 60611

4. The J. Parker

The J. Parker is a classy rooftop bar and restaurant towering high above Lincoln Park from atop the vintage Hotel Lincoln. Serving creative craft cocktails and New American fare, The J. Parker holds bragging rights to an unparalleled view of the city and a cool yet laidback vibe.

Address: 1816 N. Clark Street, the perfect vacation rental in Chicago 60614

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5. Mahalo

Tucked away in the Wicker Park neighborhood, Mahalo is a multi-level fusion eatery that offers a comfortable escape from the concrete jungle with a semblance of paradise with Hawaiian-inspired ambiance, cuisine, and boozy beverages. Featuring a dining room, two bars, and lovely rooftop patio, Mahalo welcomes patrons to sip piña coladas and munch on poke whilst admiring the Windy City from overhead.

Address: 1501 N. Milwaukee Avenue, the perfect vacation rental in Chicago 60622

Photo credit: Chicago Tribune

6. GreenRiver

GreenRiver is a modern, upscale bar and restaurant perched on the 18th-floor that overlooks the Streeterville neighborhood. The menu offers seasonal dishes and snacks as well as thoughtful cocktails derived from Irish American influence.

Address: 259 E. Erie Street, the perfect vacation rental in Chicago 60611

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7. Fountainhead

With its rooftop garden, extensive beer list, and scrumptious menu items consisting of organic, locally sourced ingredients, Fountainhead is a trendy, laid-back tavern located in the Ravenswood neighborhood. The rooftop area has a rustic charm and casual atmosphere that makes this an ideal spot to unwind over a few drinks.

Address: 1970 W Montrose Avenue, the perfect vacation rental in Chicago 60613

This article was written by Justina Tran.