Chicago’s skyline ranks among the most beautiful, and one of the best ways to appreciate it is from a rooftop high above the city. During summertime, the city’s rooftop bars come alive, showcasing panoramic vistas of Lake Michigan, the Chicago River and many of the city’s architectural masterpieces. If you’re looking for craft cocktails, a lively social scene or a luxurious sunset setting, head to these eight incredible rooftop escapes in the Windy City.
Cindy’s
The Loop · Michigan Avenue
A visit to Cindy’s has become something of a Chicago ritual. Located atop the stunning Venetian-Gothic Chicago Athletic Association Hotel, the rooftop offers prime views of Millennium Park, Cloud Gate and Lake Michigan from its glass-lined dining room and wide outdoor terrace. The crowd ranges from first-time visitors to longtime locals, and the menu features seasonal cocktails and Italian-inspired dishes and small plates such as pasta, seafood and small plates. If you’re there on a weekend, brunch is well worth the reservation, especially for dishes like the Old Fashioned French Toast and the tiger shrimp and grits.
LondonHouse
The Loop · Michigan Avenue
LH Rooftop crowns the 1923 Beaux-Arts LondonHouse Chicago with one of the city’s best vantage points. From the 22nd floor, guests can take in bird’s-eye views of the Chicago River, downtown skyscrapers and the rooftop’s famous multi-tiered triangular terrace, which has become a favorite among photographers. Time your visit for sunset, then settle in with one of the bar’s creative cocktails, whether it’s the floral Purple Rain Sangria or The Bad Bunny, which combines mezcal, Cristalino tequila, pear, ginger and mole bitters for a smoky finish.
Viceroy Chicago
Gold Coast
Pandan, the 18th-floor rooftop bar at Viceroy Chicago, brings a lush cocktail experience to Chicago’s Gold Coast. With sweeping views of Lake Michigan and the city skyline, the bar draws inspiration from Southeast Asian cuisine, featuring dishes such as lobster dumplings, Thai fried chicken and ube flan. Cocktails also offer a creative fusion with items like the Yuzu Spritz and the signature Pandan, a tequila-based drink layered with pandan, lemon, lime and subtle notes of vanilla and grass.
The St. Regis Chicago
Lakeshore East
One of the newest additions to Chicago’s luxury hotel scene, the St. Regis Chicago occupies a striking frustum-shaped skyscraper designed by renowned architect Jeanne Gang. Miru, its contemporary Japanese restaurant and lounge located on the 11th floor, draws inspiration from Japanese minimalism and Chicago Modernism, with curved architectural details, light wood finishes and an outdoor terrace with views that stretch from the Chicago River to Lake Michigan and Navy Pier. Guests can choose from an extensive wine and sake list, along with sushi, sashimi, seafood, noodle dishes and vegetable-centered specialties. A sunset visit is especially rewarding, as the city’s skyline takes on a warm golden glow.
The Gwen
Magnificent Mile
Located inside the historic McGraw-Hill Building on Rush Street, The Gwen, a Luxury Collection Hotel, Chicago puts guests in the center of one of the city’s most iconic neighborhoods. While the hotel has earned recognition as one of Chicago’s top properties and holds a Michelin Key distinction, its real appeal comes from the building’s remarkable character. The façade was designed by Gwen Lux, a pioneering female sculptor who built her career during the 1930s, when the field was largely dominated by men. Inside, Art Deco details, vintage-inspired furnishings, and modern touches preserve the glamour of Chicago’s golden age. Upstairs at The Gwen, the hotel’s seasonal rooftop bar, continues that spirit with stylish cocktails, New American shareable plates, and skyline views from its terrace.
Pendry Chicago
The Loop · Michigan Avenue
The rooftop at Pendry Chicago enjoys one of the city’s most recognizable addresses. Occupying the landmark Carbide and Carbon Building, Chateau Carbide extends the hotel’s Art Deco character to an open-air rooftop overlooking Michigan Avenue and the historic Loop. It’s an easy place to spend an evening over cocktails and conversation, with a menu of shareable bites that includes the Mediterranean Dip Trio, artisan cheese boards and a hand-carved Ibérico Ham Toast. The cocktail menu highlights bright, floral flavors with drinks such as the Lemongrass Lychee Cooler, the Dragon Fruit Watermelon Margarita and the Petals & Bitters, a refreshing combination of gin, Campari, elderflower liqueur and grapefruit juice.
Nobu Hotel
The West Loop
Nobu Hotel Chicago has a more intimate rooftop experience than many of the city’s larger venues. In the heart of the West Loop, guests can enjoy creative cocktails like the Matsuhisa Martini alongside Nobu’s signature Japanese cuisine with Peruvian influences. Menu highlights include Black Cod Miso, Yellowtail Jalapeño Sashimi, Crispy Rice with Spicy Tuna, Rock Shrimp Tempura, and Wagyu Dumplings. From the rooftop, views stretch across one of Chicago’s fastest-growing neighborhoods, where acclaimed restaurants, galleries, and new developments have turned it into one of the city’s premier dining districts.
Offshore
Navy Pier
For a rooftop experience outside of the luxury hotel scene, head to Offshore Rooftop at Navy Pier. As one of the largest rooftop venues in the country, the expansive indoor-outdoor space offers a completely different perspective from downtown’s high-rise rooftops, with open views across Lake Michigan and the Chicago skyline. The all-day menu features seafood, shareable plates, beers and creative drinks like Watermelon Sugar, made with vodka, elderflower liqueur, simple syrup, watermelon juice and lemon juice. In summer, lake breezes, live entertainment and unobstructed waterfront views make a visit to Navy Pier well worth the trip.
