Best Views of the City: 13 Rooftop Bars in Chicago You Can’t Miss

Drinking a cocktail whilst the skyline lights up around you is pretty magical. With its striking architecture and lively nightlife, Chicago is home to some of the nation’s best rooftop bars. Whether you’re looking to toast with friends, impress a date, or soak up the views, these elevated spots have more to offer than just great drinks—they provide a perspective on the Windy City you won’t forget. 

From an amazing view of the iconic Willis Tower to the shimmering water of Lake Michigan, each one offers a different part of the city’s charm. The following are 13 must-visit rooftop bars that redefine what it means to drink in style.

Cerise Rooftop

Cerise, tucked to the top of the Virgin Hotels Chicago, is the epitome of cool. This rooftop bar is full of a hip crowd as well as a quirky, artsy vibe and thrilling downtown views. The drink menu is anything but ordinary, with choices like the “Sage Against the Machine.” Cerise keeps the vibe up, whether you’re dancing to a live DJ or lounging with friends.

VU Rooftop Bar

VU is a sleek rooftop space in the South Loop with views of Chicago’s southern skyline. It’s an upscale but accessible nighttime destination with multiple bars, fire pits, and stylish cabanas. For drinks, they’ve got everything from craft beer to specialty cocktails including the “Red Sky,” with bourbon, pomegranate, and ginger. VU Rooftop Bar is ideal for a relaxed evening with friends.

Nobu Rooftop

Situated in the ever-lovely Nobu Hotel in West Loop, Nobu Rooftop is sophistication with a side of serenity. This spot has a minimalist decor and zen-like atmosphere that provides a quieter and more intimate experience. Take in views of the nearby skyline over a sake cocktail or a signature Nobu Bellini. For the ultimate indulgence, pair your drink with Nobu’s world-famous sushi.

Kennedy Rooftop

Situated in Wicker Park, the Kennedy Rooftop offers the best views of the Chicago skyline from a neighborhood vantage point. This rooftop, named after the nearby Kennedy Expressway, is casual and inviting. Favs are their “Skyline Margarita” and “Windy City Mule” to sip on while looking at the city glitz up in the distance.

AIRE

AIRE sits on the 24th floor of the Hyatt Centric in The Loop and offers panoramic views of downtown Chicago. It features a selection of cocktails, local beers, and small bites (including cheese and charcuterie, flatbreads and sliders). With its modern design and open-air layout, It’s the perfect spot for both after-work relaxation and weekend gatherings.

Utopian Tailgate

Utopian Tailgate is a playful and vibrant rooftop for anyone who wants to mix fun with fabulous views. In Old Town, this rooftop features an atmosphere reminiscent of a backyard party with its colorful decor, games, and plenty of life. Tailgate Tonic and Rooftop Lemonade are just a couple of their whimsical cocktails on the menu. This spot has you covered, whether you’re competing with friends in a game of giant Jenga or just basking in the skyline.

Z Bar

Adjacent to the Peninsula Chicago, Z Bar is all about sophistication. The outdoor terrace offers stunning views of Michigan Avenue, perfect for people-watching from above. Their menu features inventive cocktails like the “Cinema Sour,” inspired by movie theater snacks, and shareable plates like wagyu sliders. It’s the sort of place that makes you feel like a VIP.

LondonHouse Rooftop

With its perch above the historic LondonHouse Chicago hotel, this tri-level rooftop provides unrivaled views of the Chicago River, the Wrigley Building, and the streets bustling below. The outdoor terrace is the crown jewel, giving you a front-row seat to the skyline while enjoying classic cocktails like the Negroni or creative options like the LH G&T. Endeavour to arrive before sunset for a magical golden hour experience.

Cindy’s Rooftop

Overlooking Millennium Park from the top of the Chicago Athletic Association Hotel, Cindy’s feels like taking a step into a glasshouse. This spot is a hit for locals and tourists because of its panoramic views of Lake Michigan and the Art Institute. Cindy’s isn’t just about the scenery – their seasonal-inspired cocktails and shareable plates (like lobster rolls and charcuterie boards) are pretty impressive.

The J. Parker

One of the best views in Lincoln Park is from the J. Parker, sitting on top of the Hotel Lincoln. With picturesque views of the park and Lake Michigan, this rooftop is your go-to for a breezy afternoon or a romantic evening. Its retractable glass roof makes it a delightful spot to sit and enjoy craft cocktails like the Blood Orange Margarita, along with small bites like truffle fries.

Cabra

Cabra is a total gem on the rooftop of The Hoxton hotel. It offers amazing vistas of Chicago’s industrial-chic West Loop, and its Stephanie Izard’s Peruvian-inspired menu is a feast of the senses. Sip on a pisco sour or a flavorful tropical cocktail while digesting some ceviche and empanadas. It’s the sort of place where you feel you’ve discovered a secret patch of paradise in the middle of town.

The 95th

The Signature Room at the 95th is hard to beat if you’re looking for an iconic Chicago experience. This rooftop lounge is located in the John Hancock Center and soars above most of the competition, giving views across the city and beyond. Though it’s not technically ‘outdoor,’ the floor-to-ceiling windows provide an uninterrupted panorama, best enjoyed with a glass of fine wine or their classic martini.

ROOF on theWit

ROOF on theWit is known for its chic ambiance and electric vibe and is two things in one: a rooftop destination and a nightlife hotspot. It’s situated in the Loop and has dramatic city views and a bustling crowd. The bar’s award-winning mixologists whip up drinks such as the “Lavender Collins” to sip whilst looking at the glittering skyline. Don’t miss their themed nights and live music events!

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