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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

    Now Sapphire Riviera Cancun – All Inclusive

    Save up to $150 + save up to 45%

    Book a flight + hotel package and save up to $150 when you use promo code BEACHFUN150 at the time of booking. Plus, $200 in Resort Coupons. Savings vary by departure date. Book by 4/6/20 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

    Cozumel

    Grand Park Royal Luxury Resort Cozumel - All Inclusive

    Save up to $150 + save up to 50%

    Book a flight + hotel package and save up to $150 when you book with promocode BEACHFUN150 at the time of booking. Resort coupons are issued for select amenities including spa treatments, romantic dining experiences, and wine purchases. Book by 4/6/20 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.

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

    Dominican Republic, Punta Cana

    Dreams Macao Beach Punta Cana Resort and Spa - AI

    Save up to $150 + save up to 45%

    Plus, $200 in resort coupons. Book a flight + hotel package of $1,000 or more, and save up $150 when use the promo code BEACHFUN150 at the time of booking. Save $75 on packages $1,000-$2,499 or save $150 on packages of $2,500 or more. Hotel savings vary depending on date of travel. Three-night minimum stay required. 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. Book by 4/6/20 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

    Mystery Deal - Family

    Save up to 46%

    A little bit of Mystery. A whole lot of luxury. Hotel savings vary depending on date of travel and duration of travel. Book by 4/10/20 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.

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

    Cancun - Cancun Hotels

    Riu Dunamar - All Inclusive

    Save up to $400 instant savings

    Book a flight + hotel package and save up to $400 in instatnt savings when booking through Southwest Vacations. Three-night minimum stay required. Stay three or four nights and save $200; stay five or six nights and save $300; or stay seven nights or more and save $400. Book by 5/4/20 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
  • Cozumel

    Occidental Cozumel - All Inclusive

    Save up to 35% + 2 kids free

    Book a flight + hotel package and save up to 45% when you book through Southwest Vacaitons. Hotel savings vary depending on date of travel. Book by 5/4/20 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

    Barcelo Maya Beach & Caribe - All Inclusive

    Save up to $150 + save up to 40%

    Book a flight + hotel package and save up to $150 when you use promo code BEACHFUN150 at the time of booking. Plus, receive additional $200 per room, per stay in Resort Discounts. Hotel savings vary depending on date of travel. Three-night minimum stay required. The value of the resort coupons varies depending on length of stay and resort. Book by 4/6/20 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

    Iberostar Selection Paraiso Maya - All Inclusive

    Save up to 45% + 1st child free

    Book a flight + hotel package and save up to 45% at the time of booking. Plus, 1st child stays free 16 years and under free when staying with 2 paying adults. Hotel savings vary depending on date of travel. Three-night minimum stay required. Book by 5/4/20 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

    Riu Palace Costa Mujeres - All-Inclusive

    Save up to $150 + $300 in instant savings

    Book a flight + hotel package and save up to $150 when you book with promocode BEACHFUN150 at the time of booking. Plus, $200 in resort coupons when you book through Southwest Vacatios. Stay five or six nights and get $225 in instant savings. Stay seven nights or more and get $300 in instant savings. Book by 4/6/20 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

    Dominican Republic, Punta Cana

    Chic Punta Cana - AI

    Save up to $150 + save up to 70%

    Plus, VIP amenity package. Book a flight + hotel vacation packageof $1,000 or more, and save up $150 when use the promo code BEACHFUN150 at the time of booking. Save $75 on packages $1,000-$2,499 or save $150 on packages of $2,500 or more. Three-night minimum stay required. Book by 4/6/20 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®.​