Using Southwest Points for the Caribbean

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Back in January of this year, Southwest announced that they were starting service to Aruba, Montego Bay, and Nassau. This announcement had me beyond excited as I am a big Southwest fan. I have a lot of their points due to the Southwest Airlines credit card and transferring points from Wyndham Rewards (which is no longer a good option). I also hold the Southwest Airlines companion pass, so my husband flies with me for free an UNLIMITED number of times.

Within minutes of seeing this announcement I knew I’d be taking advantage at some point this year. I have never been to Aruba and it has been a winter destination I’ve wanted to check out for quite some time now (I am also excited to use my points for a free stay at the Radisson – more on that in another post). So I am now scheduled to go to Aruba over Christmas. I booked flights the day the schedule came out (you can currently book through January 4, 2015) and was able to get pretty reasonable flights being such a peak time. If I had waited even a day I would have been paying at least 50% higher. Of course I am booked on booked and the extra taxes/fees was only $72.50. I was also able to add my husband on as my companion, so he is flying almost for FREE – no points required just the taxes/fees of $72.50. Pretty good in my opinion!

Since the initial announcement of those three destinations, Southwest has in fact added a few more routes:

  • Aruba, Montego Bay, and Nassau begins on July 1, 2014
  • Cancun and Cabo San Lucas begins on August 10, 2014
  • Mexico City and Punta Cana begins on November 2, 2014

This now means you can use your Southwest Airlines companion ticket on these routes. While the companion ticket is already extremely valuable, this makes it even more worthwhile in my opinion! You can read more about the Southwest Airlines companion pass here.

I checked out the Southwest route map and currently there are none stop flights from the three destinations to the following:

  • Aruba flies direct to Orlando, Atlanta, and Baltimore
  • Montego Bay flies direct to Orlando, Atlanta, Baltimore, and Chicago
  • Nassau flies direct to Baltimore and Atlanta

Credit card to help earn the companion pass: Southwest Credit Card to help earn the companion pass: As mentioned previously, there are four different Southwest cards – ALL of them have the same bonus offer after meeting the minimum spend requirements, but different annual fees and annual bonuses. You can view all four cards and the differences in this prior blog post.  Here are the multiple ways to earn the Southwest Airlines Companion Pass.

Disclosure: This post contains some affiliate links. Thanks for supporting the blog and enjoy traveling on a deal!


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8 years ago

I have the same trip booked out of Baltimore, but over the Thanksgiving Holiday. Will also be staying @ the Radisson 4 nites, (Bogo), Wife has the CC also. Have the Southwest companion pass, and like U, saved 70% by booking early w/ miles. Also staying @ the recently renovated Holiday Inn Resort 4 nights. I consider 25K points per nite a decent redemption. Stayed @ the Marriott a few years ago but wasn’t impressed. The two hotels I mentioned are nicer and have better location. I love Club Carlson & Southwest. Both are easy to rack up the points.

Dave Golden
Dave Golden
8 years ago

Ditto. Living near BWI, Southwest is our airline of choice. The companion pass has been easy to obtain, and miles flow freely. We have our Aruba and Jamaica trips booked – as well as Vegas next week. Important to take advantage of the “19,200 pt transfer to AirTran” trick – Definitely using that when booking the tickets to Aruba.

8 years ago

Dal is our home airport…wright amendment has us screwed until nov 2…it wouldn’t be bad if they had more flights between DAL and ATL but first thing the did after getting AirTran was cut flights between hubs…so in order to fly to Caribbean we would have to go to ATL the night before and return the day after…unfortunately it doesn’t get better in Nov. there will be better connecting flights through ATL but it takes 7.5 to 8 hours to get to/from DAL to MBJ….I said to hell with the SW bus and booked a 3 hour 35 min direct flight on AA with 20,000 Avios…spending a full day (8 hours) of vacation traveling each way stinks…and while I love the companion pass, I hate the bus stop operations of SW who stop to load/unload passengers at one or two cities along the way.

Mary Beth
Mary Beth
8 years ago

So excited to for this! Six of us traveling at the cost of four due to the Companion pass to Montego bay…redeemed 250,000 AA miles for six nights and two rooms for six people at the Hilton All inclusive…best way to redeem in our case…can’t wait! Thanks for all the tips!

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