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Holiday all-inclusive trips, priced by Kristina

Real Thanksgiving, Christmas and winter prices for Mexico, the Dominican Republic and Jamaica, with flights and transfers included, plus a Florida beach week and a Scotland tour.

Prices are per person, based on two adults sharing a room, unless shown as a total. Kristina priced these on October 1, 2026 for the dates shown, with round-trip flights from Chicago and airport transfers included. Prices change often and depend on availability when you book, so she confirms the current price before anything is booked.

Mexico

Planning Mexico with Kristina

  • Le Blanc Cancun

    Thanksgiving Nov 22–30 3 nights Adults only, luxury

    from about $652 per person

    Flights + transfers included

    Ask about this trip

  • Riu Dunamar

    Thanksgiving Nov 22–30 5 nights

    from about $1,005 per person

    Flights + transfers included

    Ask about this trip

  • Riu Caribe Cancún

    Christmas From Dec 23 5 nights

    from $698 per person

    Flights + transfers included

    Ask about this trip

  • Grand Riviera Princess

    Christmas From Dec 26 6 nights

    from $925 per person

    Flights + transfers included

    Ask about this trip

  • Valentin Imperial Riviera Maya

    Christmas From Dec 27 5 nights Adults only

    from $1,198 per person

    Flights + transfers included

    Ask about this trip

Dominican Republic

Planning Dominican Republic with Kristina

  • Majestic Elegance Punta Cana

    Thanksgiving Nov 22–30 5 nights

    from $575 per person

    Flights + transfers included

    Ask about this trip

  • Majestic Colonial Punta Cana

    Christmas From Dec 23 7 nights

    from $1,199 per person

    Flights + transfers included

    Ask about this trip

  • Catalonia Royal Bávaro

    Christmas week 5 nights

    from $895 per person

    Flights + transfers included

    Ask about this trip

  • Excellence Punta Cana

    Christmas week 5 nights

    from $1,129 per person

    Flights + transfers included

    Ask about this trip

  • Ocean Blue & Sand

    Christmas week 6 nights

    from $939 per person

    Flights + transfers included

    Ask about this trip

Jamaica

Planning Jamaica with Kristina

  • The Ritz-Carlton Rose Hall

    Thanksgiving Nov 22–30 6 nights

    from $495 per person

    Flights + transfers included

    Ask about this trip

  • Couples Sans Souci

    Thanksgiving Nov 22–30 5 nights

    from $795 per person

    Flights + transfers included

    Ask about this trip

  • Holiday Inn SunSpree Montego Bay

    Christmas week 6 nights All-inclusive

    from $809 per person

    Flights + transfers included

    Ask about this trip

  • Breezes Rio Bueno

    Christmas week 5 nights

    from $975 per person

    Flights + transfers included

    Ask about this trip

  • Legends Beach Resort

    Fall and winter dates 5 nights

    from $1,329 per person

    Flights + transfers included

    Ask about this trip

  • Riu Reggae

    Fall and winter dates 5 nights

    from $1,715 per person

    Flights + transfers included

    Ask about this trip

  • Royalton Negril

    Fall and winter dates 5 nights

    from $2,069 per person

    Flights + transfers included

    Ask about this trip

Florida

  • Tropical Beach Resorts

    Nov 7–17 10 nights

    $2,587.46 for two, flights + stay

    • Stay only $2,534
    • Flights only (Chicago to Tampa) $554
    • Booked separately $3,088
    • As a package you save $500.54
    Ask about this trip

Scotland

  • Bonnie Scotland

    Many departure dates Escorted tour

    from $2,499 per person

    Flights + transfers included

    Ask about this trip

Don't see your dates?

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