These Chicago rooftop bars and restaurants boast beautiful views, refreshing cocktails, and (of course) delicious menus that cover a diverse range of cuisines and cultures. Best of all, many of them are year-round so you can enjoy rooftop vibes no matter the weather. Check out just some of Chicago’s most popular rooftop bars and restaurants.
Cindy’s
This might be the most well-known (and most Instagrammed) Chicago rooftop. Cindy’s bar and restaurant, part of the historic Chicago Athletic Association, features sweeping views of Millennium Park, “The Bean”, Michigan Avenue, and the lake. Enjoy a drink (and snap a few photos) on the outdoor terrace, then step inside the soaring, glass-enclosed dining area for elevated comfort food and more handcrafted cocktails.
Tip: The Chicago Athletic Association is home to three more bars: The Drawing Room, a cozy fireplace-filled den; the Milk Room, a micro-bar serving rare spirits; and the Game Room, a boisterous playground with billiards, bocce, and more.
Aba
It feels like summer all year long at Aba, with its abundant greenery and a light-and-airy atmosphere. But summertime is when you can snag a spot on their sprawling rooftop patio where you can order plates of fresh, seasonally inspired fare, like fresh seafood, hummus with fluffy pita, and other Mediterranean favorites.
Cabra
Stephanie Izard, the first woman to win Top Chef, expands her Chicago empire with Cabra. The rooftop Peruvian cevicheria, located in the uber-hip Hoxton Hotel, features a greenhouse feel with greenery everywhere and sunlight streaming in the all-glass wall. The dishes are just as light and airy as the vibes. The space also opens up to overlook the hotel’s rooftop pool, plus the surrounding West Loop area.
VU Rooftop
VU Rooftop offers a rare view of the Chicago skyline from the South Loop. The sleek space, located 22 stories in the air, is filled with cozy nooks, fire pits, and comfy seating to kick back and enjoy a cocktail (or two). The super-shareable menu features global influences, with everything from crispy Spanish octopus to a Nashville hot chicken sandwich.
Cabana Club
Soaring above the heart of Chicago’s collect neighborhood, Cabana Club has already established itself as one of Chicago’s hottest summer spots. It’s perched on the sixth floor of The Robey, centrally located at Wicker Park’s bustling Six Corners intersection. The hip hangout features an indoor-outdoor space, a tiny pool, chairs for sunbathing, and rare views of the city from the west.
Tanta
Is Tanta the perfect date night spot? With stylish vibes, twinkling string lights, fresh flowers, and Peruvian dishes begging to be shared, all signs point to yes. Just make sure to request a spot on their year-round rooftop. If there’s a wait, head to the large bar and order two pisco sours — your date will be instantly impressed.
ROOF on theWit
Young professionals cut loose after a long week of work at this lively rooftop lounge on the 27th floor of theWit hotel. With its modern design, glittering city views and nightclub atmosphere, it’s no wonder Travel + Leisure named it one of the top three rooftop bars in the world. Go for dishes like the stuffed scallops or grilled beef kebab, followed by a Lululemon Lemon Drop shot (vodka, fresh citrus, and lavender).
LH
Chicago’s only tri-level rooftop venue, LH Rooftop atop the LondonHouse Chicago lets guests dine on creative American cuisine and cocktails indoors or out. Expect modern design, sweeping vistas, distinctive history, and a landmark Chicago location where you can peer up and down the Chicago River.
Shanghai Terrace
The vibe: Shades of deep red and elegant Asian decor create a vintage 1930s supper club feel at this fourth-floor oasis in The Peninsula Chicago hotel that is a favorite of the well-heeled Magnificent Mile crowd. Order the Cantonese dim sum, including barbecue pork buns and spicy beef pot stickers, sided with a Lost in Shanghai (vodka, lychee, and cassis).
Boleo
The Kimpton Gray Hotel brings a luxe-modern vibe to a historic building in the heart of the Loop. The rooftop lounge on the 15th floor, Boleo, goes for sexy and sultry with its sunny, South American vibes. Enjoy Peruvian and Argentinean-inspired street food favorites and snackable small plates, while DJs pumping music under a retractable skylight roof.
Upstairs at The Gwen
This spacious rooftop feels a bit like a hidden garden. Located on the fifth floor, what this bar and lounge lacks in height, it makes up for in style. If the art deco vibe doesn’t win you over, then the Asian-inspired small plates and prosecco popsicles definitely will.
Tip: In the winter, Upstairs at The Gwen sets up a curling rink and cozy warming cabin on the rooftop.
AIRE
Feel the breeze at AIRE’s 24th-floor rooftop bar atop Hyatt Centric The Loop Chicago. This is a great low key option if you don’t want to mess with massive crowds waiting for a table. Dine on small plates made from seasonal, locally sourced ingredients and enjoy a large creative cocktail and wine menu in a chic space that wraps around the building. Soak up city views to the east, south, and west from seating that surrounds fire pits and lines along the glass walls.
Raised
This garden-in-the-sky is situated on top of the Renaissance Chicago Downtown Hotel. Raised is a hip indoor/outdoor hotel lounge on the third floor, where you’ll be high enough to enjoy the views but low enough to feel the energy of the city. Dine on shareable large plates while you gaze out at the Chicago River and the bustling Riverwalk just below.
