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Vacation Deals from Chicago

Get the most from your vacation with Exclusive Nonstop Vacation Flights. These flights are among the few, or only, nonstop options to your destination at great prices. Plus, most feature convenient morning departures and evening returns to give you the most time on the beach.
Get the most from your vacation with Exclusive Nonstop Vacation Flights. These flights are among the few, or only, nonstop options to your destination at great prices. Plus, most feature convenient morning departures and evening returns to give you the most time on the beach.

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
    Aug 25, 2025
    4 Nights Hotel + Flight From
    $565 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 25, 2025
    4 Nights Hotel + Flight From
    $777 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
    2025: Sep 20, Sep 27
    4 Nights Hotel + Flight From
    $618 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 23, Oct 21
    4 Nights Hotel + Flight From
    $611 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 20, 2025
    4 Nights Hotel + Flight From
    $752 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
    2025: Oct 27, Oct 28
    4 Nights Hotel + Flight From
    $945 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
    2025: Sep 9, Sep 16, Sep 20, Sep 23, Sep 27, Sep 30, Oct 7, Oct 11
    4 Nights Hotel + Flight From
    $598 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
    Oct 21, 2025
    4 Nights Hotel + Flight From
    $727 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
    2025: Sep 6, Sep 23, Sep 27
    4 Nights Hotel + Flight From
    $803 per person Includes Taxes + Fees

  • Bahia Principe Grand Jamaica - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive
    Jamaica, Montego Bay
    Best Priced Departure Dates
    2025: Sep 6, Sep 9, Sep 13, Sep 16, Sep 23, Sep 27, Sep 30, Oct 4, Oct 7, Oct 11, Oct 21
    4 Nights Hotel + Flight From
    $680 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.