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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 - Cancun Hotels

    Reflect Cancun - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, $200 in resort coupons and kids free. Book a flight + hotel package of $1,500 or more and save $100 when you use the promo code MAYINTHAW at the time of booking. Hotel savings vary by date of travel. Resort coupons are issued for select amenities including spa treatments, romantic dining experiences, and wine purchases. Kids free valid for travel 7/1/20-10/29/20. Book by 6/1/20 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

    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 6/1/20 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
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  • All-inclusive

    Cancun - Riviera Maya Hotels

    Secrets The Vine Cancun - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, $300 in resort coupons and free upgrade. Book a flight + hotel package of $1,500 or more and save $100 when you use the promo code MAYINTHAW at the time of booking. Hotel savings vary by date of travel. Resort coupons are per room, per stay based on resort and room categories booked. Resort coupons are issued for select amenities including spa treatments, romantic dining experiences, and wine purchases. Book by 6/1/20 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
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  • All-inclusive

    Dominican Republic, Punta Cana

    Secrets Cap Cana Resort & Spa - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, free upgrade and $300 in resort coupons. Book a flight + hotel package of $1,500 or more, and save $100 when use the promo code MAYINTHAW at the time of booking. 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. Upgrade offers are valid for travel 7/1/20-10/29/20. Book by 6/1/20 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

    Dominican Republic, Punta Cana

    Riu Palace Bavaro - All Inclusive

    Save $100 + save up to $600 in instant savings

    Plus, free upgrade and up to $2,544 in resort coupons. Book a flight + hotel package of $1,500 or more, and save $100 when you use promo code MAYINTHAW at the time of booking. Hotel savings vary depending on date of travel. Stay three or four nights and get $300 in instant savings. Stay five or six nights and get $450 in instant savings. Stay seven nights or more and get $600 in instant savings. Stay four to six nights and get up to $1,689 in resort coupons. Stay seven nights or more and get up to $2,544 in resort coupons. Free guaranteed room upgrade from Jr Suite Gardenview to Jr Suite Superior. Three-night minimum stay required. Book by 6/1/20 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

    Secrets Wild Orchid Montego Bay - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, $200 in resort coupons and free upgrade. Book a flight + hotel package of $1,500 or more, and save $100 when use the promo code MAYINTHAW at the time of booking. 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 6/1/20 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

    Ocean Coral Spring

    Save $100 + save up to 60%

    Plus, first child free. Book a flight + hotel package of $1,500 or more, and save $100 when you use the promo code MAYINTHAW at the time of booking. Three-night minimum stay required. First child free valid for travel 6/7/20-6/19/20 and 9/1/20-10/29/20. Book by 6/1/20 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

    Los Cabos

    Riu Santa Fe - AI

    Save $125 + save up to $400 in instant savings

    Plus, two kids stay free. Book a flight + hotel package of $1,500 or more, and save $100 when you book with promocode MAYINTHAW at the time of booking. Saty three or four nights and get $200 in instant savings. Stay five or six nights and get $300 in instant savings. Stay seven nights or more and get $400 in instant savings. Hotel savings vary depending on date of travel. Up to two children, ages 12 and under, stay free when staying with two paying adults in the same room. Book by 6/1/20 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

    Puerto Vallarta/Riviera Nayarit

    Reflect Nuevo Vallarta - Unlimited-Luxury®

    Save $100 + save up to 45%

    Plus, $200 in resort coupons and kids free. Book a flight + hotel package of $1,500 or more and save $100 when use the promo code MAYINTHAW at the time of booking. Hotel savings vary depending on date of travel. 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 6/1/20 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

    Aruba

    Riu Palace Aruba - AI

    Save $100 + $600 in instant savings

    Plus, up to $1,022 in resort credits. Book a flight + hotel package of $1,500 or more, and save up to $100 when you use the promo code MAYINTHAW at the time of booking. In addition, stay three or four nights and get $300 in instant savings. Stay five or six nights and get $450 in instant savings. Stay seven nights or more and get $600 in instant savings. Three-night minimum stay required. Connecting Rooms available. Book by 6/1/20 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®.​