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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
    Dec 14, 2025
    4 Nights w/Air From
    $509 per person Includes Taxes + Fees

  • Majestic Colonial Punta Cana - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    Mar 7, 2026
    4 Nights w/Air From
    $823 per person Includes Taxes + Fees

  • Riu Republica - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    2026: Sep 13, Sep 16, Sep 19, Sep 20, Sep 22, Sep 24, Sep 26, Sep 28 - Oct 1, Oct 3, Oct 13, Oct 15, Oct 16
    4 Nights w/Air From
    $455 per person Includes Taxes + Fees

  • Barcelo Maya Colonial - All Inclusive
    4.5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    2026: Sep 20, Sep 28
    4 Nights w/Air From
    $572 per person Includes Taxes + Fees

  • Riu Santa Fe - All Inclusive
    4.5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Los Cabos
    Best Priced Departure Dates
    Dec 14, 2025
    4 Nights w/Air From
    $698 per person Includes Taxes + Fees

  • Valentin Imperial Riviera Maya - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Cancun - Cancun AND Riviera Maya
    Best Priced Departure Dates
    2026: Sep 20, Sep 22, Sep 26
    4 Nights w/Air From
    $824 per person Includes Taxes + Fees

  • Sunscape Coco Punta Cana - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Dominican Republic, Punta Cana
    Best Priced Departure Dates
    2026: Sep 13, Sep 16, Sep 19, Sep 20, Sep 22, Sep 24, Sep 26, Sep 28, Sep 29, Oct 1, Oct 3, Oct 6, Oct 10, Oct 11, Oct 13, Oct 15, Oct 16
    4 Nights w/Air From
    $447 per person Includes Taxes + Fees

  • 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
    Sep 19, 2026
    4 Nights w/Air From
    $634 per person Includes Taxes + Fees

  • Riu Montego Bay - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Jamaica, Montego Bay
    Best Priced Departure Dates
    Dec 12, 2025
    4 Nights w/Air From
    $789 per person Includes Taxes + Fees
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.