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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
    Nov 11, 2025
    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
    Nov 17, 2025
    4 Nights Hotel + Flight From
    $962 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
    Dec 7, 2025
    4 Nights Hotel + Flight From
    $579 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
    Jan 25, 2026
    4 Nights Hotel + Flight From
    $600 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 8, 2025
    4 Nights Hotel + Flight From
    $675 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 13, 2026
    4 Nights Hotel + Flight From
    $1,039 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
    Dec 7, 2025
    4 Nights Hotel + Flight From
    $580 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 13, 2026
    4 Nights Hotel + Flight From
    $831 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: Nov 16, Dec 7
    4 Nights Hotel + Flight From
    $852 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.