Why I’ve Decided to Speculatively Transfer Most of My Membership Rewards Points to Hawaiian Program

I’m sure many of you know where this is going. So, we only have a few months until Hawaiian and Alaska frequent flyer programs will officially merge. It will also mean the end of Amex and Hawaiian partnership. In fact, Amex stopped transfers for awhile, though the function has been since restored.

Still, I’m sure Alaska executives aren’t too happy about this loophole. Many folks in the hobby have been busy transferring their MR points to Hawaiian, and then to Alaska Mileage Plan. You can access it via this website.

I was mildly tempted to do it when they had a 10% bonus, but decided to pass. I hate making speculative mileage transfers, as plans can change and there is always a possibility of being stuck with your stash for years. We aren’t frequent travelers, so my cost/benefit ratio calculations are done accordingly.

But my situation  has changed recently, and I’ve decided to transfer 55k Amex MR points to Hawaiian, and then to Alaska. I should mention that my MR stash was quite meager to begin with (only 75k points). Here is why I did it. Next year I’m planning to treat my daughter to a graduation trip to Japan. She liked our 2023 vacation there so much that she wants to go back (see my series of posts).

Of course, that means I will have to book flights in only a few months. We had several ideas on how we would go about it, and at one point my SIL and her husband were going to take my daughter and her friend. But everyone backed out, so it will be me taking her to Japan. I’m not complaining!

We were going to make it a girls’ only trip, but I could tell my husband was a bit sad to be left out. That surprised me, as he isn’t too keen on travel and hates long-haul flights. I asked if he would be up for it, and he said yes. Done! I prefer traveling with him anyway, despite bickering and some conflicts that inevitably arise due to jet lag. We have a dysfunctional relationship, but somehow it works.

That did create a small problem, however. Until now, I was planning to redeem AAdvantage and Alaska miles toward economy flights. I have a small stash in both programs, enough for two people. Since my husband will be joining us, I needed to come up with a quick and cheap way to increase my balances.

I don’t have any Bilt points (transfer to Alaska), and BoA has canceled my credit cards recently, just as I predicted. I’m likely banned by the bank for the foreseeable future. I will have a post on it at some point, but just want to say that I did get the funds back from my closed BoA checking account.

My husband was denied when he applied for Alaska credit card a few months ago. Ditto for Hawaiian Visa. We can’t get approved for any Citi AAdvantage credit cards, and were also denied when I tried my luck with Barclaycard Aviator. So, there goes my opportunity to accrue extra AAdvantage miles, at least on the cheap. Sure, I can always buy them for 3 cents apiece or a bit less when they go on sale. No thanks.

That leaves me with only one pathway: transfer from Amex to Hawaiian/Alaska. I value my MR points at a penny each, so this is a no-brainer compared to the alternative.

Why I’m focusing on Alaska and AAdvantage programs for flights to Japan  

Those are the only two programs that currently have a reasonable pricing on award flights to Japan, especially in economy. You can pretty much forget United and Delta unless you catch a special sale. Sure, you can use British Airways Avios (on JAL) and Virgin Atlantic (on ANA), as long as you don’t mind paying fuel surcharges. Currently, those run at $200 per person each way, which isn’t terrible, to be honest. When there is a transfer bonus, it does sweeten the deal further. However, we are talking $1,200 in fuel surcharges for three people, and that’s a big chunk of change.

Another problem is that I’m unlikely to find three seats in business class, and my husband doesn’t like the idea of splitting up and banishing our daughter to economy. We have done it, but it’s our preference to sit together if at all possible.

Of course, if you want to get a business class seat on JAL, your best bet will be going through Cathay Asia Miles program, as it gets access to those before any other partners. But we are talking lots of points and extra fees. Virgin Atlantic gets leftover business-class seats that weren’t scooped up by Lifemiles and Aeroplan users. And again, the prices aren’t necessarily all that cheap, especially compared to economy seats.

Since I already had a pre-existing stash of Alaska miles, it just made the most sense to invest in this program rather than starting from scratch elsewhere. Plus, 75k Amex MR points aren’t going to go far anyway. I do have 130k Chase Ultimate Rewards that are currently parked in my Chase Freedom Flex card, but would prefer not to convert it to a premium Chase card right now in order to unlock access to partner transfers.

Instead I transferred 55k Amex MR points to Alaska, and here is why I chose this specific amount. Since my husband is a tall guy, I’m hoping to at least treat him to premium economy for our long flight from US to Tokyo. Alaska has a sweet-spot pricing: 40k miles one-way on JAL premium economy from Seattle to Tokyo Narita. This is 10k miles cheaper than AAdvantage and British Airways Avios (the latter also has $200 in fuel surcharges).

My husband has 43k Alaska miles and I had 25k miles before the transfer. So, after MR transfer we have enough miles for three people in premium economy. Will it be available by the time Alaska program gets access to JAL seats? I honestly don’t know. But I want to be ready if/when that happens. I could roll the dice and hope that Amex MR transfer to Hawaiian survives a few more months, but that’s risky. If premium economy isn’t available, I can just get regular economy for 37.5k miles per person from any west coast city JAL flies to. Not dirt cheap, but better than spending cash.

And if my plan doesn’t work out, we can always burn Alaska miles for flights to….wait for it,  Alaska! My daughter and MIL both requested that we do a cruise to Alaska in a few years, so I’m confident that my miles won’t go to waste regardless. We will likely have to fly back from Japan to US in economy, but those flights are around 8-9 hours long, which is doable. I’m hoping to use my AAdvantage stash from Osaka to LAX at 35k miles per person. We might even be able to include a flight to Orlando the following day at no extra cost, but I’m not counting on it.

Trips to Japan are very popular right now, and the pricing reflects that. Even if you leave from LAX (usually the cheapest gateway due to competition), you are looking at over $1k per ticket in economy, and much more when you fly from Florida.

Zipair has  lower roundtrip fares on most dates, but they don’t fly to Osaka, and the cheapest seat (no food or any extras) will still run you $1k if you just want to visit Tokyo.

Final thoughts 

Miles and points are meant to be used and occasionally, you have to take a leap of faith. It definitely goes against my nature to convert highly valuable MR points to miles without knowing what award availability will be like in a few months. However, I don’t have any regrets and feel like it’s the right decision in my circumstances. Will it pay off? I have no idea, but stay tuned.

I’m super excited that my daughter caught the travel bug and chose a trip to Japan as her graduation present rather than some expensive trinket. Not to say that it will be a cheap endeavor, not at all. But I’m hoping that memories we will create as a result will be more than worth it.

It all goes by so fast. It seems like yesterday that I was writing my first post for this blog after our family trip to Canada. Time really does fly.