The Best Hotels with Rooftop Pools in Chicago

Chicago is best enjoyed from a height; its soaring skyscrapers make a striking city skyline! With a nonchalant trendy vibe, you will find many of the city's converted factories and newer glass constructions boast buzzy rooftop bars and, if you are really lucky, a rooftop pool too. The best hotels with rooftop pools in Chicago also happen to be just some of the best hotels in the city. From suave sophistication at a five-star luxury stay to chic boutiques offering that independent flare that our Hotel Gurus are so fond of. So for a spoiling city break, why not browse through our hotel experts' selection of their favourite hotels with rooftop pools?

For a boutique

• The Robey is a smart modern boutique hotel set in a striking art-deco building in Wicker Park. Pick this property for the chic whitewashed rooms (many of which have epic city views) and the French-American restaurant. However, the real pull is obviously the rooftop pool and bar.

For luxury

• The Hoxton Chicago is a hip luxury choice perfectly blending industrial and retro design. Expect vast rooms, high ceilings, polished concrete, and velvet upholstery. The range of restaurants and rooftop pool with epic views of the city skyline ensure this property won't fail to impress.
• Viceroy Chicago is a magnificent hybrid of old and new; a perfectly preserved 1920's facade attached to a glistening glass tower. Inside you will find the same paradoxes, the rooms are spectacular and so are the views from their floor to ceiling windows. The rooftop bar draws a crowd, as does The Somerset downstairs. Luxury defined.

Still not sure where to book?

• Browse our list of the best places to stay in Chicago.
• Refine your search and look at the best hotels in West Loop, Chicago.
• Check out all our recommendations in Illinois.
• Alternatively, you could contact one of our friendly Gurus for personalised advice.

  • The Robey Chicago (Wicker Park) 89 rooms from $135

    
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    City Style  -  Chic accommodation in a historic building evoking memories of bygone years

    Local exploring  -  Make the most out of The Robey's location to truly get to know Chicago

    Sights nearby  -  Head over to Wrigley Field and enjoy a Cubs game or give the Lioncoln Park Zoo a visit

    Views  -  For great views book either a Corner Suite or Panorama Suite

    

    Recommended by  -  Tablet

    Situated in Chicago's Wicker Park, The Robey is set in the art-deco former Northwest Tower building and provides boutique, upmarket accommodation. Expect fresh and contemporary design. Café Robey serves up French-American fusion cuisine and cocktails are served on the rooftop lounge. Superb! See More

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  • The Hoxton Chicago Chicago (Fulton Market) 182 rooms from $179

    
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    City Style  -  Offering a sophisticated and stylish air in an exciting, gourmet neighbourhood a short journey from the city centre

    Business meetings  -  The hotel boasts excellent meeting facilities and rooms perfectly suited for the travelling businessperson

    Local markets  -  Fulton Market takes its name from the world class food markets and dining in the area

    Sights nearby  -  The Oprah Winfrey show is filmed at the nearby Harpo Studios, a popular attraction

    

    A high-end luxury hotel in easy reach of the city centre and Chicago’s best nightlife spots, ideally designed and equipped for business or pleasure. Public spaces and rooms are bright and elegant, making excellent use of space, and the rooftop pool and range of restaurants won't fail to impress. See More

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  • Viceroy Chicago Chicago (Near North Side) 180 rooms from $214

    
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    City Style  -  A historic 1920's facade married to a glorious waved glass tower, with interiors by TAL Studio- the result will not disappoint

    Sights nearby  -  Just down the road is the Oak Street Beach, a sandy shore of Lake Michigan where one can swim and lounge in the sun

    Views  -  Great views from hotel

    Designer  -  Uniquely designed interiors.

    

    Recommended by  -  Tablet

    A magnificent hybrid of old and new, a perfectly preserved 1920's facade attached to a glistening glass tower. Inside you will find the same paradoxes, the rooms are spectacular and so are the views from their floor to ceiling windows. The rooftop bar draws a crowd, as does The Somerset downstairs. See More

    Check Availability

 

Written by Katie Harris

posted Monday, 8th February 2021