The Best Hotels With Rooftops in Chicago

The LH22 rooftop bar at LondonHouse offers you some incredible views of Chicago's skyline
The LH22 rooftop bar at LondonHouse offers you some incredible views of Chicago's skyline | Courtesy of LondonHouse Chicago / Expedia
Photo of Amy Blyth
17 November 2020

Chicago has one heck of a city skyline, featuring jagged skyscrapers, glassy offices and architectural wonders from a bygone era. Then, there’s the winding Chicago River with its buzzing waterfront and glittering Lake Michigan. There’s no better way to savor these views than by checking into one of these chic hotels with rooftops in Chicago.

LondonHouse Chicago, Curio Collection by Hilton

Suite Hotel, Luxury
4.6/5 (2659 Reviews)
Courtesy of LondonHouse Chicago / Expedia
Price Drop
Now from $103 per night
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.
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Kimpton Gray Hotel

Suite Hotel
4.7/5 (944 Reviews)
Kimpton Gray Hotel, Chicago
Courtesy of Kimpton Gray Hotel /
Price Drop
Now from $156 per night
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.
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4.4/5 (925 Reviews)
theWit Chicago
Courtesy of The Wit / Expedia
Price Drop
Now from $120 per night
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.
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The Godfrey

Independent Hotel
4.2/5 (1577 Reviews)
Courtesy of The Godfrey Hotel Chicago / Expedia
Price Drop
Now from $87 per night
The Godfrey is set on LaSalle Street in the popular River North neighborhood, boasting south-facing rooms with city views. Expect Cubist-style architecture with an industrial vein that favors geometric accents and marble floors. The Godfrey’s IO Godfrey Rooftop Lounge, set on the fourth-floor terrace, has a glass ceiling and walls that retract to give you some of Chicago’s best skyline views. Choose from an extensive drinks list, fancy sharing platters and sushi.
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Ace Hotel Chicago

Independent Hotel
4.6/5 (396 Reviews)
Ace Hotel Chicago
Courtesy of Ace Hotel Chicago / Expedia
Price Drop
Now from $139 per night
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.
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  • Virgin Hotels Chicago

    4.6/5 (1204 Reviews)
    Virgin Hotels Chicago
    Courtesy of Virgin Hotels Chicago / Expedia
    Price Drop
    Now from $155 per night
    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.
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    Thompson Chicago

    Chain Hotel, Luxury
    4.7/5 (952 Reviews)
    Courtesy of Thompson Chicago / Expedia
    Price Drop
    Now from $190 per night
    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.
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    Loews Chicago Hotel

    Suite Hotel
    4.6/5 (1399 Reviews)
    Courtesy of Loews Chicago Hotel / Expedia
    Price Drop
    Now from $126 per night
    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.
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    These recommendations were updated on November 17, 2020 to keep your travel plans fresh.

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