These Chicago hotels boast beautiful views with rooftop bars and restaurants stretched across sunny outdoor terraces. Choose your own adventure with this fresh list of venues, each giving a unique experience.
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.
This Japanese-inspired hideaway is perched atop the Conrad Chicago Hotel, just off The Magnificent Mile. String lights and fire pits create a cool and cozy vibe, and the panoramic city views don’t hurt either. The menu is globally inspired, blending Japanese and Peruvian ingredients and techniques. Don’t skip the cocktail list — we like their spiked snowballs, boozy shaved ice served in a Chinese takeout container.
Stephanie Izard, the first women 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.
Apogee’s quirky spot boasts comfortable seating, an eclectic menu of small bites, and a large-format cocktail selection served in whimsical vessels and meant for sharing. Or you could order your own drink, like the refreshing Aloe-Rita (frozen tequila, fresh lime, aloe liqueur). Whatever you choose, kick back and enjoy the surrounding River North cityscape.
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 of 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.
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.
Chicago’s only tri-level rooftop venue, 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.
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, The Gwen sets up a curling rink and cozy warming cabin on the rooftop.
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.
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.
Boleo at the Kimpton Gray Hotel
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.