Southwest Starts Flying International…But It’s Not all Good News…Yet!

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Southwest Starts Flying International…But It’s Not all Good News…Yet!

Million Mile SecretsSouthwest Starts Flying International…But It’s Not all Good News…Yet!Million Mile Secrets Team

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We’ve all been waiting for this!

You can fly to the Aruba, the Bahamas, and Jamaica on Southwest from July 1, 2014!  The Southwest schedule is open until August 8, 2014.  I’ll post an update when the schedule opens beyond August 8, 2014.

Southwest Starts Flying International But Its Not All Good News Yet
3 New Southwest Destinations From July 1, 2014!

And if you have the Southwest Companion Pass, you can bring your companion for free (pay only taxes)!

Southwest Flies to the Caribbean

Southwest and Air Tran are merging.  Air Tran used to fly to certain international destinations in the Caribbean, whereas Southwest only flew within the US and to Puerto Rico.

However, Air Tran will no longer exist by the end of 2014 and Air Tran planes will be converted to Southwest planes.

So from July 1, 2014, Southwest planes will start flying to 3 international destinations which Air Tran used to fly to.

Here are the departing and arrival cities:

From Atlanta to:

  • Aruba
  • Montego Bay
Southwest Starts Flying International But Its Not All Good News Yet
Southwest Will Fly from Atlanta to Aruba & Montego Bay

From Baltimore (Washington, DC Area) to:

  • Aruba
  • Nassau
  • Montego Bay (twice daily)
Southwest Starts Flying International But Its Not All Good News Yet
Southwest Will Fly from Atlanta to Aruba, Montego Bay & Nassau

From Orlando to:

  • Aruba (Saturday only)
  • Montego Bay
Southwest Starts Flying International But Its Not All Good News Yet
Southwest Will Fly from Orlando to Aruba & Montego Bay

What’s Next?

And by the end of 2014, Southwest should start flying their planes to other Air Tran destinations:

  • Cancun, Mexico
  • Mexico City, Mexico
  • Cabo san Lucas, Mexico
  • Punta Cana, Dominican Republic

And by 2015, Southwest should add other international destinations.

Yes, You Can Use Your Southwest Companion Pass 

You can use your Companion Pass on these new international flights!

Link:   Southwest Credit Cards

Link:   Southwest Companion Pass

Emily and I love our Southwest Companion Pass because it lets Emily fly for free for up to two years!

With the Companion Pass, when you fly Southwest, you can bring a companion for free!  Even if you pay for your flight with points!  You only pay the segment taxes (~$10).

Southwest Starts Flying International But Its Not All Good News Yet
Emily Can’t Wait to Use Our Southwest Companion Pass on an International Flight!

To get a Companion Pass, you have to earn 110,000 Companion Pass qualifying points within 1 calendar year (January 1 to December 31st).

Which can be done very easy since the 50,000 point bonus from the Southwest credit cards count towards the companion pass!  Here are 10 ways to earn the extra points needed for the Companion Pass.

All 4 versions of the Southwest credit cardsincluding the Southwest Premier card, currently offer 50,000 Southwest points after spending $2,000 within 3 months.

50,000 Southwest points are worth ~$710 to ~$850 in Southwest flights or $500 in gift cards!

Southwest’s schedule is open through August 8, 2014,  so you can book most of your summer travel.

Other Ways to Get Southwest Points

You can instantly transfer Chase Ultimate Rewards points from the Chase Sapphire Preferred, (no longer offered) Chase Ink Bold, or Chase Ink Plus to Southwest Airlines on a 1:1 ratio, if you’re running low on Southwest points.

Note that  transferring points directly from Ultimate Rewards to Southwest do NOT count towards the Companion Pass.  But you can use them for Southwest flights

Ok, But What’s not Good About Southwest Flying Internationally?

1.   You Can Only Depart From 3 Cities

For now, you can’t fly non-stop to the Caribbean unless you depart from Baltimore, Atlanta or Orlando!

Or if you are departing from Boston or Pittsburgh and connecting in the 3 international departure cities.

For example, if I search for a flight from Austin to Aruba, I get a message asking me to choose another destination.

Southwest Starts Flying International But Its Not All Good News Yet
Southwest is Testing Their Reservation System so You Can’t Fly Internationally on the Same Ticket Unless You leave from Baltimore, Atlanta, or Orlando

But I can book a flight with my Southwest points (and add a Companion) from Atlanta to Aruba!

Southwest Starts Flying International But Its Not All Good News Yet
I Could Book a Flight from Atlanta to Aruba With my Southwest Points

And  I can book a flight from Boston to Aruba with a connection in Baltimore for only 9,600 Southwest points and $15!  

Southwest Starts Flying International But Its Not All Good News Yet
But You Can Book Intenational Flights from Boston (or Pittsburgh)!

At their press conference, Southwest explained that they are still testing out their new reservation system for international passengers.

But they expect to let folks book international flights from most Southwest departure cities soon.

They also mentioned that they see certain destinations as “over-fared” and hinted at offering ticket prices lower than what was currently available!

I can’t wait for this to happen!

No Cancellation Fees & Save Points

You don’t pay a penalty to cancel a Southwest flight paid with points (the points go back to your account when you cancel), so you can book your summer travel before you confirm your plans.

You can use fewer Southwest points if you redeem your points before March 31, 2014 for flights on Southwest after March 31, 2014.

Southwest Starts Flying International But Its Not All Good News Yet
Book Before March 31, 2014 to get More From Your Points!

That’s because the cost of using points will increase for flights booked after March 31, 2014.  So your points will be worth ~15% less if you book a flight on, say, May 1, 2013 AFTER March 31, 2014.

But you will pay fewer points for the same flight if you book them with points BEFORE March 31, 2014.  And you can cancel and rebook your ticket without a fee if the number of points required for the award drops or if your plans change!

Bottom Line

You can book flights to the Caribbean on Southwest for flights departing after July 1, 2014.  However, you can’t (yet) book flights from all Southwest departure cities.  But you should be able to do so soon!

And you can use your Southwest Companion Pass on these new international flights!  The schedule is open until August 8, so you can plan international travel for only 1 month.

All 4 Southwest cards, including the Southwest Premier card, are currently offering a 50,000 point sign-up bonus which is worth about $710 to $850 in Southwest flights or $500 in gift cards!

If you liked this post, why don’t you join the 25,000+ readers who have signed-up to receive free blog posts via email (only 1 email per day!) or in an RSS reader …because then you’ll never miss another update!

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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Flying from Atlanta to Jamaica with a lay over in Orlando. Do I check in international

Hi Daraius and all, I’d like some advise if any one can help- I have the Southwest Premier Rapid Rewards Visa Signature card in good standing which I’ve had for three years. I’d like to get a Southwest Air Companion Card (starting January of next year- 2016) so it would be good for almost two years- 2016 through 2017. As the Rapid Rewards miles (I would need 110000 miles to get the Companion Card) need to be collected in one calendar year- I would need to apply for two new SWA Cards (in January) and that accumulate 10000 more miles? Getting 10000 miles is not a problem but should I close my present SWA Visa Signature Card now (September of 2015) to have a better chance of getting two new cards and then apply for the two new cards in January or should I just try and get two new cards from SWA (actually Chase Bank). My credit scores are 800’s but I think they (Chase) would question why I need three SWA branded cards. Any and all reponses are greatly appreciated. Right now I have 15735 points in this year (2015) towards Companion Pass status.

Sent in September 22, 2015

Jeffrey Beardsley

As of this morning, 03/17/2015, Southwest still does not offer service from MCO to MBJ (Orlando to Jamaica). I have to go back up to Baltimore. Ain’t gonna happen. Bummer. And they profess not to have any information as to when it will start. Oh well.

We have flown Southwest many times but wish they would at least go through the summer months including August. Why the cut the service off after July is Crazy! Either you fly to a destination or you don’t!

The reservation system is still very clunky as of January 2015. I tried to book from Islip, NY to Aruba (going thru BWI) but instead have to book separate flights, Islip to BWI landing around 7:30 am and BWI to Aruba taking off around 9 am. You would think someone at Southwest would have considered this before opening up the international market for reservations.

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