Chicago Deals

Chicago Vacation Packages

 from $619
 
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.
 

Up to $100 OFF per booking with Marriott Hotels & Resorts

  • $100 OFF stays of 5 nights or more
  • $75 OFF 4-night stays
  • $50 OFF 2- and 3-night stays
  • Book by 7/22/18 for travel through 10/31/18
All Deals Include: Round-trip airfare, Hotel accommodations, Taxes and more

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.

    • Traditional Double
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $649+

    Boston, MA (BOS) departures, valid for travel 09/08/18

  • 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 hotel is nestled in the heart of the restaurant and theatre districts where guests can find plenty of things to do in downtown Chicago.

    • Deluxe City View King
    • Exclusive $50 Off per booking
    • Stays of 5 nights or longer receive $100 Off per booking
    • Kids 17 & younger stay FREE

    3 nights with flight from $794+

    Boston, MA (BOS) departures, valid for travel 09/08/18

US Cities and Canada - EXCLUSIVE up to $100 OFF per booking with Marriott Hotels & Resorts offer: Valid on new bookings made 6/11 - 7/22/18 for travel 6/11 - 10/31/18. Minimum 2-night hotel accommodations at participating Marriott hotel and roundtrip air required. Savings is $50 off stays of 2-3 nights, $75 off stays of 4 nights and $100 off stays of 5 nights or longer. Savings is per booking, taken at time of booking and reflected in rate shown. Certain restrictions apply.
Rates quoted are per person, based on double occupancy unless otherwise stated. Rates for other travel dates may vary. Rates, terms, conditions and itinerary are subject to availability. Certain restrictions apply. Rates shown include government-imposed fees and taxes. Airline fees for optional services, including, but not limited to, baggage fees, may apply. Airline tickets are non-refundable and subject to airline change/cancellation penalties and rules, including pre-flight notification deadlines. Fees and policies vary among airlines and are subject to change without notice. Please contact the airline directly for details and answers to specific questions you may have. Additional restrictions apply. Advertised rates do not include any applicable daily resort or facility fees payable directly to the hotel operator at check-out; such fee amounts will be advised at the time of booking. Where applicable, kids stay free in same room as adults using existing bedding. Occupancy limits apply. Where applicable, kids eat free with full paying adult. Not responsible for errors or omissions. [Pleasant Holidays acts only as an agent for the various travel providers shown above.]