[Disclosure: Emily and I get a commission for some of the cards in this post. You don't have to use our links, but we're very grateful when you do!]
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.
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:
- Montego Bay
From Baltimore (Washington, DC Area) to:
- Montego Bay (twice daily)
From Orlando to:
- Aruba (Saturday only)
- Montego Bay
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
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).
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.
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, 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.
But I can book a flight with my Southwest points (and add a Companion) from Atlanta to Aruba!
And I can book a flight from Boston to Aruba with a connection in Baltimore for only 9,600 Southwest points and $15!
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.
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!
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.
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