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Vacation Deals from Chicago
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Exclusive Nonstop Vacation Deals from Chicago O'Hare

Exclusive Nonstop Vacation Deals from Chicago O'Hare

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  • Grand Oasis Cancun - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Apr 12, 2026
    4 Nights Includes Taxes + Fees
    $717 per person

  • Majestic Colonial Punta Cana - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    2026: Nov 15, Nov 16, Nov 29, Nov 30
    4 Nights Includes Taxes + Fees
    $1,016 per person

  • Riu Republica - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Aug 23, 2026
    4 Nights Includes Taxes + Fees
    $730 per person

  • Barcelo Maya Colonial - All Inclusive
    4.5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Sep 1, 2026
    4 Nights Includes Taxes + Fees
    $726 per person

  • Riu Santa Fe - All Inclusive
    4.5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Los Cabos
    Best Priced Departure Dates
    May 10, 2026
    4 Nights Includes Taxes + Fees
    $936 per person

  • Valentin Imperial Riviera Maya - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Aug 29, 2026
    4 Nights Includes Taxes + Fees
    $1,036 per person

  • Sunscape Coco Punta Cana - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    2026: May 3, May 5, May 9, May 12
    4 Nights Includes Taxes + Fees
    $645 per person

  • Dreams Sands Cancun Resort & Spa - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    Aug 29, 2026
    4 Nights Includes Taxes + Fees
    $761 per person

  • Riu Montego Bay - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Jamaica, Montego Bay
    Best Priced Departure Dates
    Feb 22, 2026
    4 Nights Includes Taxes + Fees
    $954 per person
We're sorry; there are no hotels that match the criteria you have selected.
*Availability and pricing varies by room category and length of stay. Valid for bookings made 8/11/23-8/24/23 for travel 8/20/23-10/26/23.