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.

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^®.​