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Find low fares on international 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.
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.
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.
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.
Whether your idea of fun is sitting on a beach with a drink in hand or careening through the rainforest via zip line, this tropical gem has you covered.
Combine the historic charm of Old San Juan with the high-end shops of Condado, and throw in sparkling beaches, renowned restaurants, and eclectic hotels. ¡Aqui vamos!
*Our tropical destinations have country-specific travel policies and restrictions unique to the destination. Here's a list of documentation required to check out before booking and traveling.
Travel Advisory
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our COVID-19 Travel Information page for information about potential restrictions on air travel.
Your trip comes with low fares and no hidden fees. That's Transfarency®.
We want to make your trip special, so we're taking everything you love about Southwest and bringing it all to your travels. Get everything Transfarency has to offer on your next trip, only with Southwest.
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.
International travel tips
If you’re new around here, we’re so happy to have you. Flying with us is easy and fun—this guide is your one-stop shop for doing things the Southwest way.
We’ll be waiting to welcome you with free snacks and countless smiles, so we want to get you onboard as quickly and smoothly as possible!
Our tropical destinations have country-specific travel policies and restrictions unique to the destination. Here's a list of documentation required to check out before booking and traveling.
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).
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.
