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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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  • TripAdvisor Traveler Rating
    Reviews
    • Accessible Resort
    JOIA Rose Hall by Iberostar (Formerly Iberostar Grand Rose Hall) - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Aug 25, 2025
    3 Nights Hotel + Flight From
    $945 per person Includes Taxes + Fees
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    Reviews
    Includes savings up to 40%
    Breathless Cancun Soul Resort & Spa - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Cancun - Cancun AND Riviera Maya

    Best Priced Departure Dates
    Jul 28, 2025
    3 Nights Hotel + Flight From
    $724 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    Reviews
    JOIA Bavaro by Iberostar (Formerly Iberostar Grand Bavaro) - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Aug 8, 2025
    3 Nights Hotel + Flight From
    $861 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    Reviews
    Riu Republica Adults Only - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Aug 17, 2025
    4 Nights Hotel + Flight From
    $621 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    Reviews
    Riu Palace Punta Cana - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Aug 23, 2025
    4 Nights Hotel + Flight From
    $725 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    Reviews
    Royalton CHIC Punta Cana, An Autograph Collection - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Jul 28, 2025
    3 Nights Hotel + Flight From
    $572 per person Includes Taxes + Fees
  • Nonstop Vacation Deals
    Includes savings up to 38%
    Complimentary non-stop transfers included
    Hotel Xcaret Arte - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Cancun - Cancun AND Riviera Maya

    Best Priced Departure Dates
    Aug 28, 2025
    3 Nights Hotel + Flight From
    $1,320 per person Includes Taxes + Fees
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    Reviews
    Includes savings up to 45%
    Includes up to $500 in resort credits
    Iberostar Waves Quetzal - All Inclusive
    4 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Cancun - Cancun AND Riviera Maya

    Best Priced Departure Dates
    Aug 28, 2025
    3 Nights Hotel + Flight From
    $612 per person Includes Taxes + Fees
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    Reviews
    Special discounted rates
    Live Aqua Beach Resort Punta Cana - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Aug 1, 2025
    3 Nights Hotel + Flight From
    $874 per person Includes Taxes + Fees
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    Reviews
    Includes savings up to 40%
    Limited time steal of a deal
    Breathless Punta Cana Resort & Spa - All Inclusive
    5 Star Hotel
    TripAdvisor Traveler Rating
    Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Aug 8, 2025
    3 Nights Hotel + Flight From
    $738 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.