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

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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  • All-inclusive

    Cancun - Riviera Maya Hotels

    Breathless Riviera Cancun Resort & Spa - Unlimited-Luxury®?

    Save $200 + $200 in resort coupon

    Plus, fifth night free, free upgrade and free night certificate for return stay when book five nights or more. Book a flight + hotel package of $500 or more, and save $200 when use the promo code 200INTL20 at the time of booking. Resort coupons are issued per room, per stay. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Jamaica, Montego Bay

    Secrets Wild Orchid Montego Bay - Unlimited-Luxury®

    Save $200 + $200 in resort coupon

    Plus, sixth night free, free upgrade and free night certificate for return stay when book six nights or more. Book a flight + hotel package of $500 or more, and save $200 when use the promo code 200INTL20 at the time of booking. Resort coupons are issued per room, per stay. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
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  • All-inclusive

    Jamaica, Montego Bay

    Grand Palladium Lady Hamilton Resort & Spa - Al

    Save $200 + save up to 40%

    Plus, $1500 in resort credit. Book a flight + hotel package of $500 or more and save $200 when use the promo code 200INTL20 at the time of booking. Hotel savings vary depending on date of travel. Guests will receive a resort credit of $1500 per room per stay. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Los Cabos

    Dreams Los Cabos Suites Golf Resort & Spa - Unlimited-Luxury®

    Save $200 + $200 in resort coupon

    Plus, fourth night free, free upgrade and free night certificate for return stay when book four nights or more. Book a flight + hotel vacation package of $500 or more and save $200 when using the promotion code 200INTL20 at time of booking. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Up to two children 12 and under stay free when staying with two paying adults in the same room. Kids free offer valid 8/16/20-12/22/20. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Nassau/Paradise Island - Nassau, Bahamas

    Melia Nassau Beach - AI

    Save $200 + save up to 45%

    Book a flight + hotel package of $500 or more, and save $200 when you use promo code 200INTL20 at the time of booking. Hotel savings vary by date of travel. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Cancun - Cancun Hotels

    Grand Oasis Cancun - All Inclusive

    Save $200 + save up to 67%

    Plus, VIP inclusions and free night offers. Book a flight + hotel package of $500 or more and save $200 when use the promo code 200INTL20 at the time of booking. Hotel savings vary depending on departure date. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Cancun - Riviera Maya Hotels

    Royalton Riviera Cancun Resort & Spa - AI

    Save $200 + save up to 69%

    Plus, couples massage and up to $600 resort coupons. Book a flight + hotel vacation package of $500 or more, and save $200 when use promo code 200INTL20 at the time of booking. Hotel savings vary depending on date of travel. Complementary couples massage valid in Diamond Club categories with four-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    3 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Jamaica, Montego Bay

    Royalton Negril Resort & Spa - AI

    Save $200 + save up to 71%

    Plus, couples massage and up to $600 resort coupons. Book a flight + hotel vacation package of $500 or more, and save $200 when use promo code 200INTL20 at the time of booking. Hotel savings vary depending on date of travel. Complementary couples massage valid in Diamond Club categories with four-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Jamaica, Montego Bay

    Secrets St. James Montego Bay – All Inclusive

    Save $200 + $200 in resort coupon

    Plus, sixth night free, free upgrade and free night certificate for return stay when book six nights or more. Book a flight + hotel package of $500 or more, and save $200 when use the promo code 200INTL20 at the time of booking. Resort coupons are issued per room, per stay. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure dates
  • All-inclusive

    Cancun - Riviera Maya Hotels

    Now Sapphire Riviera Cancun – All Inclusive

    Save $200 + save up to 45%

    Plus, fifth night free, free upgrade and free night certificate for return stay when book five nights or more. Book a flight + hotel vacation package of $500 or more and save $200 when using the promotion code 200INTL20 at time of booking. Resort coupons are issued for limited discounts on select amenities including spa treatments, a romantic dining experience, and wine purchases. Up to two children 12 and under stay free when staying with two paying adults in the same room. Kids free offer valid 8/16/20-12/22/20. Three-night minimum stay required. Book by 8/26/20 by 6:00 p.m. CT. Like this deal, but want more flexibility? Look for the Search More Options link to change your length of stay.

    5 nights hotel + flight from
    $ 0 total per person
    View departure 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®.​