Southwest Airlines Caribbean Flight Guide

If you’re planning a Caribbean trip on a budget, choosing the right airline is important, and flying with Southwest Airlines is one of the best ways to do it, as the airline offers low fares, no change fees, and two free checked bags. Traveling the Caribbean on a budget.

Curious about how a Southwest Airlines flight to the Caribbean works? Here’s a detailed rundown of what you can expect.

The Caribbean islands offer a diverse range of scenery and activities, and Southwest makes it easy to explore them all.

If you’re heading to the Caribbean with Southwest Airlines, you can book the following flights:

It’s useful to know which airports Southwest Airlines flights to the Caribbean stop through. If you want to fly directly to the islands, you’ll need to depart from one of these airports:

For example, let’s say you want to fly to Aruba in May, but you live in Seattle. You can’t fly directly from Seattle, but you can book a flight to Baltimore-Washington International Airport (BWI) and catch a connecting flight from there. To do so, you’ll need to factor a stopover into your travel plans, which may be necessary if there are no direct flights from your local airport.

When booking a Southwest Airlines flight to the Caribbean, you should check flight availability on the airline’s low-fare calendar to ensure that your selected dates fit within the flight’s operating schedule.

Southwest Airlines doesn’t operate daily flights to every Caribbean destination, and in fact, availability for departure and return flights can vary widely depending on your location and desired travel dates.

For example, let’s say you’re planning a winter vacation and want to fly round trip from Atlanta (ATL) to Punta Cana (PUJ). You look at Southwest Airlines’ low fare calendar and see that there are no departing flights available until mid-March.

However, if you book the same trip from Atlanta to Punta Cana in May, the departure flight will only be on a Saturday, but the return flight can be booked for any day that month.

Your departure and arrival points may also affect flight availability. For example, if you’re traveling from Baltimore (BWI) to Aruba (AUA) in May, you’ll see that there are more flights to choose from when looking at the low fare calendar compared to options from Atlanta to Punta Cana in May.

Southwest Airlines fares to the Caribbean vary depending on your origin, destination, and travel dates. You can book Southwest flights with either points or cash.

Going back to our Atlanta to Punta Cana flight example above, we can see that it’s much cheaper to book a flight in early May than in late May. Fast forward to July and we can see that fares are even more expensive.

This assumes you pay in cash, but keep that in mind. Rapid Rewards MembershipThe number of points required to book an award ticket varies depending on travel dates and destination.

For a trip to Punta Cana, you’ll need 7,800 points to book a flight departing in early May, but if you book around July 1st, you’ll need 14,742 points.

Please note that the price does not include applicable taxes or fees, even if you book using points.

On the plus side, Southwest has a reputation for being affordable – there are no change fees and the first and second checked bags are free – but you’ll still be responsible for the 7.5% federal excise tax, the $4.10 federal interstate fee, the $5.60 one-way security fee and any passenger facility charges imposed at the airport.

Southwest Airlines has slightly different check-in procedures for international and domestic flights.

If your itinerary includes at least one international flight, online check-in is available from 24 hours to 90 minutes before your flight’s scheduled departure.

You’ll need to check in online to secure an early boarding position, but you’ll also need to check in at the Southwest Airlines airport ticket counter in order for your passport to be checked and for you to receive your boarding pass (and check your bags, if necessary).

Southwest recommends arriving at the ticket counter at least two hours before your flight’s scheduled departure. If you arrive less than 60 minutes before departure, Southwest will not allow you to board. Additionally, for flights departing from Aruba, you must arrive an additional 75 minutes before or you may be denied boarding.

In addition, all passengers (including U.S. citizens and children, regardless of age) must possess a valid passport to travel to and from the United States.

If you want to save money on your Southwest Airlines flight to the Caribbean, the right travel rewards card can help. Southwest offers several co-branded credit cards that allow you to earn points on purchases and earn free flights.

Not only do you earn points on your Southwest purchases, but these cards also allow you to earn points on all other purchases. When comparing cards, first determine whether a personal or business card is right for you. Then, consider the annual fee and card benefits to help you choose the right card.

Southwest Airlines is one of the top budget airlines in the United States, so if you’re interested in low-cost flights or don’t mind giving up some business or first-class amenities, flying to the Caribbean may be an attractive option. With Southwest Airlines, you can visit multiple Caribbean destinations, 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 towards free flights to the Caribbean islands faster.