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Best Staycation Hotels Chicago

Discover the best hotel staycations in Chicago

1-9 of 9 results
  • The Robey

    The Robey is a stylish design boutique hotel in Chicago, Illinois. Situated near Wicker Park, the cool 4-star hotel occupies two distinct buildings. One is a grand limestone Art Deco building from 1929, while the other is an old fireproof…
  • Chicago Athletic Association Hotel

    Chicago Athletic Association Hotel is a gorgeous historic boutique hotel in the Downtown Chicago. The luxury 4-star hotel is housed inside a Venetian Gothic-style building, designed by Henry Ives Cobb in 1893 as a private athletic club. In collaboration with…
  • The Hoxton Chicago

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    The Hoxton Chicago is one of the best boutique hotels in the Fulton Market District of Chicago. The cool 4-star hotel is housed inside a 12-story complex with a brick facade and warehouse-style windows. Led by the in-house team, the…
  • Pendry Chicago

    Pendry Chicago is one of the best luxury boutique hotels in Downtown Chicago. Located in The Loop, the luxury 4-star hotel is housed inside the iconic Art Deco Carbide & Carbon Building from 1929. Echoing the building’s gorgeous black facade,…
  • Viceroy Chicago

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    Viceroy Chicago is one of the best luxury boutique hotels in Downtown Chicago, Illinois. Working with architecture studio Goettsch Partners, the 5-star hotel revived the former Cedar Hotel in the Gold Coast district. The building’s original brick-and-terra-cotta facade has been…
  • Kimpton Gray Hotel

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    Kimpton Gray Hotel is an elegant boutique hotel in Downtown Chicago, Illinois. Located inside the heart of The Loop, the upscale hotel is housed inside a historic granite building, previously home to New York Life Insurance. Echoing its grand facade, the…
  • SOPHY Hotel

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    SOPHY Hotel is a modern boutique hotel on the southern side of Chicago. Tucked away in the heart of Hyde Park, the upscale hotel occupies a modern industrial-style building. Contrasting the red brick and metal facade, the interior features a…
  • Hotel EMC2

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    Hotel EMC2 is a distinct boutique hotel in the Streeterville neighborhood of Downtown Chicago, Illinois. Set inside a narrow black modern building, the hotel is anything but conventional. Designed by Rockwell Group, the interior is funky and playful, with heavy…
  • Nobu Chicago

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    Nobu Chicago is one of the best luxury boutique hotels in Downtown Chicago, Illinois. Situated inside a warehouse-style building in Fulton Market, the 5-star hotel showcases an opulent modern design with a traditional Japanese twist. For instance, the interior features…

The Best Staycation Hotels In Chicago

Some of the best staycation hotels in Chicago include the Chicago Athletic Association Hotel, Kimpton Gray Hotel, The Robey, Pendry Chicago, The Hoxton Chicago, Viceroy Chicago, and more. For instance, the Chicago Athletic Association Hotel is a boutique hotel with a cool historic charm, while The Hoxton Chicago and Viceroy Chicago are upscale hotels with rooftop pools.

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