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Our Best Deals from Chicago

Save up to 70% on your next all-inclusive vacation.
Save up to 70% on your next all-inclusive vacation.

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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
    2025: Sep 30, Oct 28
    4 Nights Hotel + Flight From
    $546 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
    Oct 27, 2025
    4 Nights Hotel + Flight From
    $799 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
    Oct 20, 2025
    4 Nights Hotel + Flight From
    $602 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
    2025: Sep 30, Oct 28
    4 Nights Hotel + Flight From
    $608 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
    Oct 6, 2025
    4 Nights Hotel + Flight From
    $728 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
    Sep 28, 2025
    4 Nights Hotel + Flight From
    $995 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
    Oct 20, 2025
    4 Nights Hotel + Flight From
    $530 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
    Dec 2, 2025
    4 Nights Hotel + Flight From
    $745 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
    Sep 30, 2025
    4 Nights Hotel + Flight From
    $848 per person Includes Taxes + Fees
We're sorry; there are no hotels that match the criteria you have selected.