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Southwest Air fly to Puerto Rico

Why Southwest Air Is The Best Airline To Fly To Puerto Rico

We have been flying to and from Puerto Rico for 3 years now. This year alone, we flew to/from San Juan six times. We’ve flown to USA, USVI, and Europe and after many different airlines we came to the conclusion that Southwest Air is the best airline for flying to Puerto Rico. During our trips, we had tried American Airlines, JetBlue, Spirit (never again!), Iberia, Southwest, and Delta.

Our best experiences have consistently been when we flew Southwest.

Consider this story:

On our last trip back to San Juan, we found ourselves sitting on the runway for over an hour in Tampa and started to wonder what was going on. “There is a problem with one of our engines, folks”, said the captain. “We will need you to de-plane, while we get another craft brought in to fly you to San Juan”.

What?! Shit!

We then proceeded to wait another 3 hours at the airport before the plane was fixed. Yes, I said fixed, we never got another craft to fly us home. We arrived in San Juan at 1:30 in the morning, rather than the scheduled 9:00 PM.

This was Southwest Air. Why then do we still think they are the best airline to fly to and from the island?

Here is why:

  • Flexible Scheduling
  • Reliability
  • Inexpensive Fares
  • Two free checked bags
  • Great boarding system
  • Nice point system on their credit card
  • Lots of destinations
  • Fantastic Online Booking system

Flexible Scheduling

This is perhaps the biggest plus for us with Southwest. No need for flight insurance because you worry about your plans changing. Southwest Air allows you to reschedule your flight up to 1 hour before takeoff. That is not a typo. Seriously – 1 hour.

On numerous times, we booked a flight several months in advance and then our schedule changed, so we needed to reschedule or cancel. This was no problem with Southwest. We simply logged in online and changed/cancelled our flight. No fees, no fuss. Simple and painless. This is true even of their cheapest fares “Wanna get away”, the fare may not be refundable but it is easy to reschedule and fee-free. We love that flexibility with Southwest.

easy button

Southwest Air Is Reliable

In the story above, Southwest gave each and every passenger a $100 voucher toward any Southwest flight to make up for the inconvienience. And I mean any flight for anyone. The vouchers were basically like cash. But that’s not what makes the airline great. Things happen and mechanical problems occur on planes, this is not news. However, Southwest has still been the most reliable, on time airline, we’ve ever flown. In fact, some flights leave early. Nope, not kidding. It is not uncommon for flights to board all the passengers and if everyone is on board early, the flight leaves early. This has happened to us twice in the past two years when flying from Florida.

According to Airline Quality Ratings, on-time performance of Southwest Air continues to improve, at 79.7% for 2015 it was an improvement of 3.5% from the previous year. And, the involuntary denied boardings performance is well above average for the industry.

Southwest Air Is Inexpensive

Southwest is a budget airline. It is a no frills, no fluff type of experience. If you want superb 1st class service, Southwest is probably not the airline for you. But for a budget airline, it is excellent.

It got its start in Dallas, Texas with just three jets. Today the company owns more than 700 planes and in, 2014 & 2015 it was one of top 2 carriers by volume of domestic passengers.

Clearly, others like what Southwest offers too. The airfares are really well priced, especially if you fly mid-week. You can also get some phenomenal special deals. Recently, I compared flights on Southwest to flights on Delta. The flight we needed was $414 on Southwest, while on Delta the flight was $705. This is a big difference to us.

Two Free Checked Bags

How many airlines do you know that will give you two (2) free checked bags on domestic flights? Hell, most international flights don’t even give you two. If you are moving to Puerto Rico, this is especially nice.

When we moved here, we came down the first time with 4 suitcases (2 each) and then a second time with 4 more. This was a nice savings to having to ship stuff. Very convenient and a stark difference to other budget airlines. Even full service airlines, like United are doing away with free checked baggage (and carry-on too!) these days, so I appreciate Southwest even more for this policy alone.

Great Boarding System

I love that it is a first come first serve system! No assigned seats. The earlier you check in (online), the better boarding position you will get. This system is far more efficient than the assigned seat systems other airlines use.

Here is how it works:

“We have a quick, easy, and efficient boarding process. Look at your boarding pass to find your assigned boarding group (A, B, or C) and boarding position (1 – 60). When your group is called, stand by the column with your number on it until it’s your turn to board.”

After that, you simply choose whichever seat is available. You can also upgrade your boarding position to section A, for an additional charge.

Credit Card Point System

Southwest Visa card is one of the best airline point cards out there. During one of their promotions, you can get up to 50,000 bonus miles when you sign up. That’s equivalent to about 4 round-trip tickets! And you earn points on every purchase on your card. In addition, the more you fly, the more you earn.

They have companion ticket specials, as well. If you fly a lot, this card is worth looking into. See more info at Southwest Airlines Rapid Reward Visa site.


If you’re wondering about where Southwest Air flies, check out the map below. That’s pretty impressive.

Southwest Air Destinations


Source: Southwest Airlines

With their acquisition and merger of AirTran Airline, Southwest has expanded their destinations by 21 cities. Many of which are in the Caribbean International market. And yes, Southwest does fly to Cuba, they just haven’t been promoting it as much as JetBlue.

Fantastic Online Booking system

In my opinion, this is the best thing about Southwest: their website. It is amazingly easy to book a flight with credit card or their point system. It is equally easy to check-in online, print your boarding passes, and pretty much do anything you need to do.

I love that you can set up a login account and link it to your Southwest Rewards Visa card to have it be your default form of payment. I also love that you can login and change and cancel your flights online. It’s all straight forward and easy, I can’t tell you what a huge contrast it is to Spirit Airlines’ crappy online system!

So, there you have it. This is why we think that Southwest is the best airline to fly to Puerto Rico. We have had really good luck with them and we do have their credit card. Over the past 2 years, we’ve earned 6 free flights. That’s pretty good, isn’t it?



About Joanna

is a Polish American living in Arizona with her husband Tim. She is a founding partner of JTR Tech and she is proud to be a professional geek. She had dreamt of living abroad for many years. So, she and Tim created AbroadDreams.com to document the process of making their dream of moving abroad come true. They spent 2 years in Puerto Rico and several months in Spain and Poland. Now they are exploring the American Southwest.

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  1. I would like to fly on Southwest but the lack of assigned seats worries me. I have severe anxiety so I need to be in an aisle seat near the exit and/or bathroom. I’m afraid I would never be able to get that seat. :/ I absolutely hated flying on Easyjet in Europe because of that (plus people are jerks and push their way to the front of the line.)

    • Hi Jenn,
      I’d recommend that you pay a little extra (it’s still quite cheap) for the Early Bird Check-in, it puts you in the first group of people loading the plane. This way you can choose the best seat you like.

  2. What a terrific article, Joanna! I don’t need the info for now, but I got “drawn into” reading it because you wrote it so well: no muss, no fuss; pretty much how you described Southwest Airlines. They should PAY YOU for writing go glowingly about them!