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A Dilemma: Burn Southwest Rapid Rewards Points or Use Companion Fare Deal from Alaska Credit Card?

As I’ve mentioned last Thursday, Southwest schedule was finally extended through August 6th, 2018. I have been eagerly anticipating this development because I needed to book my flight from San Francisco to Orlando (the last leg of the epic journey to South Pacific).

Originally, I planned to use 2for1 deal from my Alaska co-branded credit card (more details in this post). Virgin America has been folded into the brand, and they happen to have a non-stop flight from SFO to MCO. Unfortunately, the time of the departure is not that great:

That means we would have to wake up at around 5:30 AM in order to make the flight, factoring in transfer to the airport. Since we will be recovering from the horrible 14 hour economy flight from Sydney, this is not ideal, to say the least.

Yes, we would get into Orlando at a reasonable time, which is a plus, though there is an issue there as well. My brother-in-law is supposed to pick us up from the airport and he will be working, since we will be flying on a weekday. We live two hours form Orlando, so he would have to quit at 2:30 PM. I really hate asking people to rearrange their work schedule in order to accommodate us.

Also, the price of the flight isn’t all that cheap, even when  factoring in BOGO deal. That would make it $135 per person. A good deal, sure, but not earth-shattering, especially when you consider the drawbacks I’ve mentioned. I started looking into other options.

Southwest introduces San Jose-Orlando route

I’ve read an announcement that Southwest will be flying non-stop from San Jose to Orlando, starting next summer. It does take an hour to get to SJC airport from downtown area in San Francisco (compared to 25 minutes to SFO), but this option seemed intriguing. But what about schedule, as well as price? It appears that this may be a better option for us compared to Virgin America:

That’s 9,697 Rapid Rewards points, plus $5 in taxes. I speculatively value this amount at around $116 (based on 1.2 cents valuation), so we are looking at a price of  $121 per ticket compared to $135 on Virgin America. We can also check in our bag for free on Southwest. Obviously, the cost of the longer transfer will eat up the savings, so it will probably end up being a wash.

The reason I like Southwest option better is the fact that the flight leaves at noon. That means that factoring in our one hour ride to the airport, we can still  sleep in till 8:30 AM. I have no idea what type of jet lag we’ll be dealing with, so it may be better to go with this option, just in case. Also, my BIL won’t have to worry about leaving work early in order to pick us up from the airport. While I dislike  the idea of such a late arrival, I dislike getting up at 5:30 even more.

A nice thing about Southwest is that you can cancel your reservation and get the points fully refunded. So for now, I’ve decided to just go ahead and get those flights reserved. I did use my Southwest gift card in order to pay $11 in taxes, and will lose that amount if I choose to cancel the flight.

Well, technically, I would have a travel credit, but I don’t think we would use it before expiration. The rules are different when you pay with a credit card because the amount is refunded back to your account. But I can live with losing $11. If the price of Virgin America flight comes down considerably, I may be persuaded to go with that option instead.

A third option

As many of you know, SFO is a hub of United Airlines. While I don’t have any United miles, I do have a leftover Avianca stash (their Star Alliance partner). I burned most of what I had  on our Sydney-San Francisco tickets, but chose to hang on to the rest of the  miles in case I need to fly home to Belarus at the last minute. For that reason I would be inclined to leave them alone.

However, if low-level award seats (12,500 miles per ticket) become available, I would at least consider burning them. United has two non-stop flights to Orlando: at 9 AM and 1 PM. Neither is ideal, but at least we wouldn’t have to deal with a long drive to San Jose  airport. For now, I only see economy tickets for 25,000 miles each, so it’s a no-go at this point.

Wait, is there actually a fourth option?!

After booking my SJC-MCO route, I’ve noticed that Southwest will start flying to Orlando from Oakland as well (tickets cost 11,000 points per person). Hmm, it’s considerably closer to downtown San Francisco than San Jose airport, but the departure is at 9:00 AM. So many things to consider, my head is spinning. Whatever option I choose, I’m sure it will end up backfiring!

We will probably be up at 4:00 AM anyway, and I will feel like a total idiot for booking a later flight and schlepping all the way to San Jose. Looking at all the options, I will likely stick with Southwest. In my experience, the crew on the planes  is always incredibly friendly and eager to help.

While I look at the price/routing/departure times first and foremost, good customer service does make a difference. I like to be treated like a human being. Who doesn’t? My sister-in-law loves Southwest so much, she opted for connecting flights to LAX rather than booking a non-stop option on another airline. I must admit, this is when I’m compelled to “cheat” on my favorite carrier.

But I’ve been a huge fan of Southwest program for a long time. The simplicity of redeeming points and customer-friendly refund policy make it a no-brainer for a regular family like mine. And as you can see, their prices are very often competitive compared to the other guys. You can see more information on Chase Southwest co-branded credit cards here, though I would hold off applying for now because the bonus will likely be raised to 60k points in the future.

If you are new to this hobby and don’t fall under 5/24 rule, you may want to consider applying for Chase Sapphire Preferred or Chase Ink Business Preferred card (if you happen to have a business). The points you earn from the sign-up bonus transfer to Southwest on 1:1 basis. Both of the cards  pay us commission if you want to support the site.

Readers, if you have flown to Australia, what is the jet lag like coming back? Do you think I’m making the right choice by booking a noon flight on Southwest?

P.S. If you have a decent stash of transferrable Ultimate Rewards points and are looking to redeem Alaska Companion certificate, make sure to read this post on Travel Codex.  I imagine the same strategy would work with FlexPerks, as well as Citi Thank You points, but I’m not 100% positive.

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Author: Leana

Leana is the owner and founder of Miles For Family. She enjoys beach vacations and visiting her family in Europe. Originally from Belarus, Leana resides in central Florida with her husband and two children.

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4 thoughts on “A Dilemma: Burn Southwest Rapid Rewards Points or Use Companion Fare Deal from Alaska Credit Card?

  1. I feel like your speculative valuation of the SW points is (a) an underestimate and (b) more importantly, unfounded.

    SW points (if booked for Wanna Get Away fares) are generally worth 1.4-1.6cpp, with higher value coming from cheaper flights.

    In your example, you don’t even need to speculate on the value of the SW points because you can literally compare it to the current going rate for the exact same SW flight to see what value you’re getting

    I’m not sure which exact flight you were looking at but this one is incredibly similar with numbers that can’t be too far off:
    Monday July 16th from SJC -> MCO leaving at 12:05PM and getting in at 8:10PM costs $158.98 or 9720 RR points.

    From that alone, you could argue that that amount of RR points is worth ~$159 because that’s what you would pay in cash for the same flight and you don’t need to even use the CPP.

    Just for fun if you wanted to calculate the CPP:
    (Cash price of flight – Fees for reward) / # of points = cent per point valuation:
    ($158.98 cash price -$5.60 cost of reward booking) / 9720 RR points = $0.0158 / RR point = 1.58 cpp (much higher than your speculative valuation of 1.2cpp).

    • WLW, I apologize for your comment originally going to spam. Not sure why that happened, but my spam plugin does crazy stuff sometimes. I understand what you are saying and don’t disagree with your valuation. Yes, I’m aware that I can get 1.5 cents per Rapid Rewards point RIGHT NOW. The problem is, we don’t plan to fly for a long time after the trip to South Pacific. So, I have to take that into consideration.
      It’s hard to say what Southwest currency will be worth THEN, hence my conservative valuation NOW. Makes sense? I guess the way to look at it is this. If I offered you my Rapid Rewards points for 1.5 cents each, would you buy them?
      Additionally, when we do decide to fly, there may be other better/cheaper/more convenient options. Southwest points are not flexible currency where you can burn them on any airline. Well, technically, you can if you have their co-branded credit card. But in that case, you will only get 1 cent per point. That’s why I don’t think it’s fair to value my Southwest points based on what that can get me on Southwest-operated flights right now. However, if I were a frequent traveler who constantly flies Southwest, it would be another matter.
      I do think you brought up an interesting point. Perhaps a separate post on this topic is in order. Thanks for stopping by!

  2. I would much rather pay a little extra in points for airport convenience than spend more time traveling to another airport. As for your brother-in-law picking you up, couldn’t you hang out at the airport after you arrive so he can pick you up at a convenient time for him?

    • @Stephanie I hear you. My biggest concern is the time of the departure. It stinks to add an extra 30 minutes to our commute, but it will be a one-time thing. I thought about booking Oakland-Orlando tickets on Southwest speculatively, but they have gone up to 13,000 Points per person. I know we will need some time to recover from the Sydney flight. Decisions decisions…

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