Chicago Deals

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.
 
  • W Chicago Lakeshore
    W Chicago Lakeshore
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

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

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  • The Westin Michigan Avenue Chicago
    The Westin Michigan Avenue Chicago
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This elegant hotel on the Magnificent Mile offers easy access to upscale shopping at Water Tower Place.

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  • Sheraton Grand Chicago
    Sheraton Grand Chicago
    Magnificent Mile, Chicago, IL Our 4-Star classification designates those properties with well-appointed, deluxe accommodations, extensive amenities and comprehensive guest services. Expect attention to detail and a warm and hospitable staff ready to cater to your needs. These superb properties offer a truly refined getaway.

    This chic hotel is ideally located in the heart of downtown Chicago, overlooking the Chicago River.

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  • Four Seasons Hotel Chicago
    Four Seasons Hotel Chicago
    Magnificent Mile, Chicago, IL Our 5-Star classification designates those select properties that provide exquisite service and amenities. The discriminating traveler will find the accommodations, ambiance, dining, and staff assistance of the highest caliber. These properties offer the utmost in luxury and will provide an outstanding experience.

    Rising from downtown Chicago’s Magnificent Mile, this luxury hotel offers unrivaled views of Lake Michigan and the Chicago skyline, accompanied by award-winning hospitality.

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  • DoubleTree by Hilton Chicago-Magnificent Mile
    DoubleTree by Hilton Chicago-Magnificent Mile
    Magnificent Mile, Chicago, IL Our 3.5-Star classification designates those properties where guests experience an ideal mix of comfortable accommodations and modern amenities. Most of these hotels feature a variety of services, and offer distinguished style and comfort. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    This comfortable hotel is just two blocks from Michigan Avenue and the Magnificent Mile, offering easy access to Chicago’s most popular attractions.

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