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.
 
  • Four Seasons Hotel Chicago
    Four Seasons Hotel Chicago
    Downtown Chicago 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 city skyline, accompanied by award-winning hospitality.

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  • Sheraton Grand Chicago Riverwalk
    Sheraton Grand Chicago Riverwalk
    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 Sheraton Grand Chicago Riverwalk is ideally located in the heart of downtown Chicago, overlooking the Chicago River.

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  • The Drake Hotel
    The Drake Hotel
    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 acclaimed hotel is an elegant symbol near Oak Street Beach at the onset of Chicago's Magnificent Mile, affording guests easy access to the city's most exclusive shopping, nightlife and dining.

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  • The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
    The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
    Magnificent Mile, Chicago, IL Our 4.5-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. Half star indicates that the hotel/resort meets all criteria of the designated rating and exceeds in certain areas.

    Awarded TripAdvisor’s Traveler Choice 2023 Award and The MUSE Hotel Awards, this hotel embraces Chicago’s 1930s vintage glamour and contemporary elegance. With lively experiences and social events throughout the hotel, let this luxury hotel be the launchpad for your Chicago experience.

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  • Hilton Chicago
    Hilton 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.

    Integrated into the Chicago skyline, this hotel near Grant Park rewards guests with the opportunity to immerse themselves within the city's architectural roots.

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