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Chicago to Cancun Deals
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Deals from ORD Airport to Cancun

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  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $500

    Dreams Aventuras Riviera Maya - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Jan 8, 2027
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $885 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $500

    Dreams Aventuras Riviera Maya - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Dec 2, 2026
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $815 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun

    Hyatt Vivid Cancun - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Jan 8, 2027
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $867 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun

    Hyatt Vivid Cancun - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Dec 14, 2026
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $824 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $500
    Exclusive Offer

    Dreams Tulum Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Mar 2, 2027
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $913 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $500
    Exclusive Offer

    Dreams Tulum Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Dec 14, 2026
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $823 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $300
    Exclusive Offer

    Riu Palace Kukulkan - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    2027: Jan 17, Jan 18, Jan 25
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $936 per person
  • TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $300
    Exclusive Offer

    Riu Palace Kukulkan - All Inclusive - Adults Only
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    Dec 14, 2026
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $807 per person
  • Nonstop Vacation Deal
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    Cancun
    Instant Savings up to $300
    Exclusive Offer

    Riu Palace Riviera Maya - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    TripAdvisor Reviews
    All-Inclusive
    Round-Trip Flights Included
    Best Priced Departure Dates
    2027: Feb 22, Mar 1
    3 Nights Hotel + Flights Hotel + Flight + Taxes & Fees
    From $1,054 per person
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*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.