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.
 
  • 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.

    Book Now
  • Palmer House a Hilton Hotel
    Palmer House a Hilton 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 iconic downtown hotel offers guests the grandeur of tradition with an infusion of elegance.

    Book Now
  • Radisson Blu Aqua Hotel, Chicago
    Radisson Blu Aqua Hotel, Chicago
    The Loop Downtown 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.

    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.

    Book Now
  • 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.

    Overlooking Lake Michigan, this hotel affords the feeling of being miles away from anything despite its proximity to Navy Pier and sitting within reach of Chicago's many attractions.

    Book Now
  • Hilton Chicago O'Hare Airport
    Hilton Chicago O'Hare Airport
    Chicago O'Hare, Illinois 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.

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

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