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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.
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
This destination currently has a travel restriction in place that may impact your trip.
Re-entry into the United States: All Passengers traveling from an international destination will require proof and verification of a negative COVID-19 test obtained within three days of travel or will be denied boarding. Visit our COVID-19 Travel Information page for more information.
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.
Why fly Southwest®?
Bags fly free®1
Your bags fly free, because no golf bag3 or swimsuit should be left behind. So pack up without paying up with our two free checked bags.
No change fees2
Think your plans may change? Don’t sweat it. We don’t charge you fees to change your mind2.
Gate to gate WiFi4
Surf the Web before you surf the waves with gate-to-gate WiFi on your flight. Bring your device, and the internet will make time fly by on our flights to tropical destinations.
Fly in comfort
Southwest seats give you up to a 31-inch pitch, 17-inch width, and 2-inch recline, which all adds up to a more comfortable flight.
100% free entertainment.
Boredom doesn’t fly with us. So on your flight, watch a movie4 for free. Just one way we make getting to your tropical destination as nice as being there. Well...almost.
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.
3A golf bag can be substituted for one checked bag.
4Download the Southwest® app to view movies and on-demand content. Inflight messaging only allows access to iMessage and WhatsApp. Apps must be downloaded before the flight. Internet access for $8 a day per device on WiFi-enabled aircraft. Price is subject to change. May not be available for the full duration of flight. Prohibits access to high-bandwidth applications and websites, including Netflix, HBO GO® and VoIP, along with certain obscene/offensive content.
