In a city that boasts some of the world’s most iconic skyscrapers, there’s something special about sipping a craft cocktail on a rooftop bar overlooking the stunning Chicago skyline. Chicago’s rooftop bars offer an unparalleled experience, with panoramic views of Lake Michigan, Wrigley Field, and the city’s architectural masterpieces. Whether you’re a local or a visitor, these rooftop bars are a must-visit destination for anyone looking to experience the best of Chicago’s nightlife.

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The Best Rooftop Bars in Chicago

From modern designs to historic landmarks, Chicago’s rooftop bars offer a unique blend of style and substance. Here are our top picks for the best rooftop bars in Chicago, each with its own unique character and charm.

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Roof on TheWit

Located on the 27th floor of TheWit Chicago, Roof on TheWit is a modern rooftop bar that offers stunning views of the city. With its floor-to-ceiling windows, pulsating beats, and big-time energy, this rooftop bar is the perfect spot to enjoy a cocktail and take in the breathtaking views of the city. The menu features a range of globally-inspired dishes, from spicy pea puree to lobster and shrimp tacos dorados.

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One of the standout features of Roof on TheWit is its retractable roof, which offers a unique and unforgettable experience. Whether you’re enjoying a cocktail or dining on the menu, the retractable roof provides an unparalleled view of the city. The bar also features a range of handcrafted cocktails, including the State & Rare, with banana-infused tequila, orange, and orgeat, and the Magnificent Spritz, with kiwi and apple-infused gin, elderflower, and cucumber.

Upstairs at the Gwen

Located on the rooftop of the Gwen hotel, Upstairs at the Gwen is a stylish and intimate rooftop bar that offers stunning views of the city. With its lounge seating, upbeat tracks, and greenery, this rooftop bar is the perfect spot to relax and unwind. The menu features a range of flavorful dishes, from garlic shrimp with Spanish chorizo to hand-cut pappardelle with pecorino and basil.

One of the standout features of Upstairs at the Gwen is its fire pits, which offer a cozy and inviting atmosphere on chilly winter nights. The bar also features a range of handcrafted cocktails, including the North Ave. Beach Party, with rose, strawberry, and lime, and the Lou’s Diner Martini, with n/a coffee liquor, espresso, and cream.

Courtesy Streeterville Social

Located on the third floor of the Loews Hotel Chicago, Streeterville Social is a lively and refreshing rooftop bar that offers stunning views of the city. With its string lighting, lush plant sections, and sweeping skyline views, this rooftop bar is the perfect spot to enjoy a cocktail and take in the breathtaking views of the city. The menu features a range of globally-inspired dishes, from beef tenderloin sliders to lobster and shrimp tacos dorados.

One of the standout features of Streeterville Social is its ‘We Drink Pink’ promotion, which takes place every Wednesday and benefits the American Cancer Society. The bar also features a range of handcrafted cocktails, including the frozen North Ave. Beach Party, with rose, strawberry, and lime, and the Lou’s Diner Martini, with n/a coffee liquor, espresso, and cream.

Offshore Rooftop

Located at historic Navy Pier, Offshore Rooftop is a unique and unforgettable rooftop bar that offers stunning views of the city. With its floor-to-ceiling windows, pulsating beats, and big-time energy, this rooftop bar is the perfect spot to enjoy a cocktail and take in the breathtaking views of the city. The menu features a range of globally-inspired dishes, from spicy pea puree to lobster and shrimp tacos dorados.

One of the standout features of Offshore Rooftop is its retractable roof, which offers a unique and unforgettable experience. Whether you’re enjoying a cocktail or dining on the menu, the retractable roof provides an unparalleled view of the city. The bar also features a range of handcrafted cocktails, including the State & Rare, with banana-infused tequila, orange, and orgeat, and the Magnificent Spritz, with kiwi and apple-infused gin, elderflower, and cucumber.