The Best Hotels With Rooftops in Chicago

The LH22 rooftop bar at LondonHouse is loved for its 360-degree views of Chicago’s skyscraper-studded skyline. Set along the Chicago River and overlooking Michigan Avenue, the bar is a favorite for evening cocktails. When the property was built in 1923, it was one of the area’s big four skyscrapers and home to an insurance company. Enjoy vintage design flair, with black and gold accents and floor-to-ceiling windows, as well as a spa, fitness center and restaurants.

Check into the Kimpton Gray, a newer addition to Chicago’s hotel portfolio. Set in an 1894 Art Deco skyscraper in the Loop neighborhood, the hotel is made from Georgia gray marble (hence the name), with high ceilings and twin lobby staircases. The 15th-floor rooftop bar Boleo is a highlight, thanks to its retractable glass roof for drinks under the stars, accompanied by resident DJs and urban views. Boleo serves South American street food, including ceviche and tacos – best to be washed down with pisco sours.

With a lightning bolt slashed across its glass façade, theWit certainly makes its mark on Slate Street. The Four Diamond hotel has an even more unusual interior, with a snazzy lobby and eye-catching artwork. There are a gym and yoga studio for guests, as well as a spa and restaurant. It’s the award-winning ROOF bar on the 27th floor that really packs a crowd though, especially in summer, for its downtown views, retractable roof and innovative cocktails.

The Waydown rooftop lounge at Ace, named for a song by Illinois musician John Prine, has supreme views of the downtown skyline. Styled on midwestern bars, the indoor and outdoor lounge hosts DJs at night and serves craft beers, cocktails and snacks. Ace has become a hipster staple, set in a former Italian-American cheese factory. There’s also a co-working space in the lobby, the City Mouse tapas restaurant and a basement gym. Its Bauhaus design reflects the trendy West Loop area.

Entrepreneur Richard Branson brings you his first hotel, set in the former Old Dearborn Bank Building, which is known for its ornately carved façade. The hotel occupies a prime location just a few minutes from Michigan Avenue, which provides spectacular views from the rooftop lounge, Cerise. Its outdoor wooden deck is dotted with comfy sofas, and DJs pump music nightly. The hotel has a 1920s vibe, with brass doors, red carpets and pet-friendly rooms that have separate sleeping and living areas.

The award-winning Thompson Chicago is known for its stylish, industrial design. Think wood and leather with copper chandeliers and iron staircases. Rooms have bright velvet furniture and floor-to-ceiling windows to show off views of Lake Michigan and the city. The Penthouse Terrace Suite offers incredible views of the high-rises and skyscrapers of Chicago’s skyline. Enjoy the suite’s loft-style layout, which boasts a separate seating area and a soaking tub.

Loews is home to Streeterville Social, one of Chicago’s most talked-about rooftop terraces. The huge deck showcases downtown urban views and is packed in the summer. There’s a full drinks list, accompanied by food and music. Stay at Loews for contemporary rooms with picture windows, local artwork and a star location near the river and Michigan Avenue. There’s also a spa and an authentic Argentine steakhouse, Rural Society.