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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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.