Exclusive pricing on flight + hotel packages.
All-inclusive vacation deals from Chicago (Midway) to Mexico and the Caribbean.
Southwest Vacations
® is perfect for new adventures because the amazing exclusive 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. There are also lots of additional deals with the Vacation Exclusive packages listed below. 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.
Prices below are only valid when departing from Chicago (Midway).
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Cancun - Cancun Hotels
Riu Palace Peninsula - AI
Save up to $150 + up to $300 in instant savings
Valid departure date(s):
2/23 - 9/1
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Hotel Rating
Luxury: exceptional accommodations, superior service and a full range of amenities
Superior: deluxe accommodations, excellent service and a wide variety of amenities
Standard: pleasant accommodations, good service with many amenities available
Modest: comfortable accommodations with some services and amenities
Basic: simple accommodations with few services and amenities
TBD
Hotel rating to be determined
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.
^Prices shown are per person based on double occupancy and include all airport, flight, and hotel taxes and fees except resort fees which are charged by the hotel upon arrival. Prices are valid for flight + hotel packages for the length of stay listed above to either Cancun (CUN), Punta Cana (PUJ), or Jamaica via Montego Bay (MBJ) with departures from Chicago (MDW) on the departure dates listed above. Pricing may differ when traveling from other origins, for longer than the length of stay shown, to different hotels not listed, or on dates not listed above.
†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. The Mark Travel Corporation is the tour operator for Southwest Vacations.