Southwest® flights to the Caribbean.

Jet off to a locale as diverse as your interests—the songs of the islands dotting the Caribbean Sea are calling.

Visit the Caribbean.

When you visit the Caribbean, you’ll quickly recognize that no two islands are alike—though they may all have gorgeous sugar-sand beaches in common. From dancehall beats and reggae vibes to infectious salsa sounds, vibrant communities lure you to their island homes. Enjoy and discover vibrant histories, burgeoning modern urban settings, authentic foods, art unlike anything you’ve encountered before, and, of course, the unparalleled beaches. What are you waiting for? Your flight to the Caribbean is ready to be booked.

Featured destination.

Montego Bay

Dive into island life with a trip to Montego Bay. Both exotic adventure and luxurious relaxation abound on the island of Jamaica, and Montego Bay has plenty of both to suit every traveler. Dance to the island beat while you pack your bag for your Jamaican vacation.

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Caribbean destinations

Island hopping awaits. Underwater adventures, mountain views, diverse cultural influences, and more are at your fingertips—or just dig your toes into the white sand beaches.

Aruba

Immaculate beaches and turquoise waters draw people to this idyllic Dutch island, but the friendly residents and vibrant international culture are what keep them coming back.

Join Rapid Rewards®, our award-winning frequent flyer program¹.

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No blackout dates.

You can use your points to book any seat, on any flight, no exceptions. Any day, any time, any flight, your points are ready to take you to where you want to go.

Your points don’t expire.

You can earn points on flights and on everyday purchases with our partners, which makes getting to our tropical destinations easy. No matter when, or where, you earn them, your points won’t expire.

¹2016-2020 Freddie Awards.

The check-in process is a little bit different for international travel. Learn more here.

The U.S. Customs and Border Protection allows expedited clearance for pre-approved, low-risk travelers upon arrival. If you’d like to breeze through security a little easier, you may be interested in Global Entry. You can apply here.

Save time at U.S. Customs and Passport control checkpoints when you download the Mobile Passport app by Airside Mobile (available in select cities).

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