Chicago skyline and shore of Lake Michigan

Chicago Vacation Packages

 
The third most populous city in the United States, Chicago sits perched on Lake Michigan, its skyscrapers glistening above the horizon. The iconic John Hancock Center, sky-high Willis Tower and Tribune Tower rise above the city's nearly three million residents.
 
  • Magnificent Mile, Chicago, IL Our 4-Star

    This acclaimed hotel commands a pride of place on Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

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  • Magnificent Mile, Chicago, IL Our 4-Star

    This iconic downtown hotel offers guests the grandeur of tradition with an infusion of modern elegance.

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  • The Loop Downtown Our 4.5-St

    Dive into the rich culture of downtown Chicago from this striking hotel located in the heart of the city and just minutes from top attractions.

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  • Magnificent Mile, Chicago, IL Our 4-Star

    The only hotel overlooking Lake Michigan, the W Chicago - Lakeshore is close to Navy Pier and the city's many attractions.

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  • Chicago O'Hare, Illinois Our 3.5-St

    Just steps away from all domestic terminals at O'Hare International Airport, this hotel is ideal for savvy travelers.

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Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]