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All-inclusive vacation deals from Chicago (Midway) to Mexico and the Caribbean.

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Southwest Vacations® is perfect for new adventures because of our amazing deals on packages. The kind of vacation deals that include all-inclusive resorts and flight options from Chicago Midway International Airport with plenty of convenient nonstop flights to Mexico and the Caribbean. So why not check them out? There are plenty of Southwest Vacations vacation packages just for you when flying out of Midway airport. Learn more about all-inclusive vacation packages and destinations like Cancun, Riviera Maya, and Puerto Vallarta. Or, you can always create a customized vacation package that includes perks like airport transfers, attractions, amenities, excursions, tours, and much more.

Didn’t find the right fit? Don’t worry about it. You can always explore vacation deals to any of Southwest Vacations destinations.

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  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Breathless Cancun Soul Resort & Spa - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 24, 2025
    5 nights hotel + flight from
    $1,139 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Dreams Sands Cancun Resort & Spa - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 31, 2025
    5 nights hotel + flight from
    $1,021 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Riu Palace Las Americas Adults Only - All Inclusive

    4.5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    2025: Jul 16 - Aug 31
    7 nights hotel + flight from
    Get Price
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Breathless Punta Cana Resort & Spa - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Dominican Republic, Punta Cana
    Best priced departure dates
    2025: Aug 24, Aug 25
    4 nights hotel + flight from
    $1,080 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Royalton CHIC Cancun, An Autograph Collection - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 24, 2025
    5 nights hotel + flight from
    $1,103 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Planet Hollywood Cancun, An Autograph Collection - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 31, 2025
    5 nights hotel + flight from
    $1,065 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Grand Park Royal Luxury Resort Cancun - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 24, 2025
    5 nights hotel + flight from
    $806 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Riu Palace Kukulkan Adults Only - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    Aug 24, 2025
    5 nights hotel + flight from
    $1,023 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Breathless Cancun Soul Resort & Spa - All Inclusive

    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun AND Riviera Maya
    Best priced departure dates
    Aug 25, 2025
    4 nights hotel + flight from
    $974 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews

    Grand Oasis Cancun - All Inclusive

    4 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive
    Cancun - Cancun Hotels
    Best priced departure dates
    2025: Jul 16 - Aug 31
    3 nights hotel + flight from
    Get Price
Not seeing deals? Modify your travel preferences, change your destination, or select new dates.

Customized vacation packages include:

  • Roundtrip flight via Southwest Airlines® from Chicago (Midway) to Cancun (CUN), Riviera Maya via Cancun, Punta Cana (PUJ), or Jamaica via Montego Bay (MBJ).
  • Hotel accommodations (including taxes).
  • Bags fly free®† with Southwest Vacations. Even golf bags fly free®.

Learn more about the benefits of booking with Southwest Vacations.

†First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Hotel surcharges may apply to weekends, holidays, and convention periods. Flights available on published, scheduled service only. Rates may be subject to change until purchased. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. ALG Vacations Corp. is the tour operator for Southwest Vacations®.​