A Guide to Southwest Flights to the Caribbean

You can book Southwest's international flights to the Caribbean for less than 8,000 points each way.

Rebecca LakeJan 19, 2021
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If your travel plans include booking a Caribbean getaway on a budget, your choice of airline matters. Given Southwest’s low fares, lack of change fees and two free checked bags, flying Southwest is one of the best ways to travel to the Caribbean on a budget.

Southwest Airlines flies to a number of Caribbean destinations, including some very popular tourist spots. If you're enrolled in the Rapid Rewards program, you can redeem your points to book flights and/or earn bonus points when you book your trip with a Southwest co-branded credit card.

Curious about how Southwest flights to the Caribbean work? Here's a closer look at what you can expect.

Where Southwest flies in the Caribbean

The Caribbean islands feature a diverse mix of scenery and things to do, and Southwest makes it easy to explore all they have to offer.

When you fly Southwest to the Caribbean, you can book flights to:

  • Grand Cayman, Cayman Islands.

  • Havana, Cuba.

  • Montego Bay, Jamaica.

  • Nassau, The Bahamas.

  • Oranjestad, Aruba.

  • Providenciales, Turks and Caicos.

  • Punta Cana, Dominican Republic.

  • San Juan, Puerto Rico.

Image courtesy of Southwest

Fly direct

It's helpful to know which airports Southwest flights to the Caribbean will take you through. If you want to fly direct to the islands, you'll need to depart from one of these airports:

  • Baltimore-Washington International Airport (BWI).

  • Chicago Midway International Airport (MDW).

  • Denver International Airport (DEN).

  • Fort Lauderdale-Hollywood International Airport (FLL).

  • Hartsfield-Jackson Atlanta International Airport (ATL).

  • Nashville International Airport (BNA).

  • Orlando International Airport (MCO).

  • St. Louis Lambert International Airport (STL).

  • Tampa International Airport (TPA).

  • William P. Hobby Airport (HOU).

Say you wanted to fly to Aruba in May, but you live in Seattle. You couldn't fly directly out of Seattle, but you could book a flight to Baltimore-Washington International Airport (BWI), then make a connecting flight from there. Doing so may mean factoring a layover into your travel plans, but that may be necessary if you're not able to fly direct from your local airport.

Flight availability

When booking Southwest flights to the Caribbean, you'll need to check the airline's low-fare calendar for flight availability to ensure your chosen dates can be accommodated by its flight operating schedules.

Southwest doesn't always operate flights to individual Caribbean destinations daily — in fact, the availability for departure and return flights may differ significantly across locales and desired travel dates.

By dates

For example, say you wanted to schedule a winter getaway and fly round-trip from Atlanta (ATL) to Punta Cana (PUJ). A look at Southwest's low fare calendar shows no available departure flights until mid-March.

However, if you were to book the same trip from Atlanta to Punta Cana for May, you'd see that you could only fly out on a Saturday, but you could book your return flight for any day of the month.

By destination

Your departure destination and arrival location may also influence flight availability. For example, say you're departing from Baltimore (BWI) and traveling to Aruba (AUA) in the month of May. A look at the low-fare calendar shows there are more flights to choose from compared to the Atlanta to Punta Cana options in May.

Booking Southwest flights to the Caribbean

Southwest fares to the Caribbean can vary based on where you're departing from, where you're traveling to and your travel dates. You can use points or cash to book Southwest flights.

Expect dynamic pricing

If we go back to the example of the Atlanta to Punta Cana flight mentioned earlier, you'll see that it's much cheaper to book flights in early May versus late May. Fast-forward to July, and you'll see fares peaking even higher.

That's assuming you're paying cash, but remember — you can also use points to book if you're a Rapid Rewards member. The amount of points you'll need to book an award flight depends again on your travel dates and destination.

For the Punta Cana trip, you'd need 7,800 points to book a departure flight at the beginning of May, but if you book around the first of July, you'd need 14,742 points instead.

Expect to pay fees for both cash and award fares

Keep in mind that even when you book with points, the prices don’t include applicable taxes and fees.

On the bright side, Southwest has a reputation for being fee-friendly. There are no change fees and your first and second checked bags fly free. But you're still responsible for federal excise tax of 7.5%, a $4.10 federal segment fee, a $5.60 security fee per one-way trip and airport-assessed passenger facility charges.

Checking in for your Southwest Caribbean flight

The check-in process is a bit different on Southwest’s international flights versus domestic flights.

If your itinerary includes at least one international flight, online check-in is available as early as 24 hours and as late as 90 minutes before your flight’s scheduled departure time.

While you should check-in online to secure an early boarding position, everyone must also check-in at Southwest’s airport ticket counter to have passports verified and receive boarding passes (and, if necessary, to check luggage).

Southwest recommends arriving at the ticket counter at least two hours prior to your flight’s scheduled departure. Arrive with less than 60 minutes to go, and Southwest won’t allow you to board. Or, if you’re on a flight departing Aruba, you must arrive an even longer 75 minutes in advance — or may be denied boarding.

Additionally, all passengers (including U.S. citizens and children, regardless of age) must have a valid passport book in order to travel to and from the United States.

Earn points faster with a credit card

If you're interested in saving money on Southwest flights to the Caribbean, the right travel rewards card can help. Southwest offers several co-branded credit cards to help you rack up points toward free flights on purchases.

Card options include:

Aside from earning points on Southwest purchases, each of these cards allows you to earn points on everything else you spend. When comparing cards, first decide whether a personal or business card is more appropriate. Then consider the annual fees and card benefits to help you choose the right one.

If you want to fly Southwest to the Caribbean

Southwest is a top-rated economy airline in the U.S. and the option to fly to the Caribbean may be appealing if you're interested in low-cost flights or don’t mind foregoing business- or first-class amenities. You can visit multiple Caribbean destinations when flying Southwest, and flights can be booked with cash or Rapid Rewards points.

Joining the Rapid Rewards program and opening a Southwest Airlines credit card can help you earn points toward free Caribbean flights faster.


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