Taking a chance on Alaska miles — the reason I applied for two Hawaiian Airlines cards on the same day

I’m likely one of the most credit card-reliant members of the TPG team. I have so many cards that keeping track of them requires me to use spreadsheets for managing all my benefits. In fact, I currently have over 20 active cards.

Considering my existing number of cards, I hadn't been looking for another one ... until Alaska Airlines revealed its plans to acquire Hawaiian Airlines in December 2023.

Alaska has stated that it will continue to run Hawaiian Airlines as a distinct brand while merging the Alaska Airlines Mileage Plan and HawaiianMiles into a single loyalty program. This creates the potential for HawaiianMiles to eventually become valuable Mileage Plan miles ... or something akin to that. This motivated me to start accumulating some HawaiianMiles right away.

The proposed merger reached a significant milestone in August 2024 when the Department of Justice announced it wouldn't intervene to block the deal. However, it still requires approval from the Department of Transportation. Alaska Airlines stated that the merger "... remains contingent on the U.S. Department of Transportation (DOT) granting an interim exemption for the transfer of international route authorities." The DOT has yet to provide a timeline for its decision.

Nonetheless, DOT approval is generally regarded as the less significant of the two main obstacles to finalizing the deal.

Regardless, I established my credit card strategy late last year, well before the regulatory process began.

I recognize that opening two credit cards based on a potential scenario is quite speculative on my part. Nevertheless, I value Alaska miles highly and believe there's a sufficient chance that this hypothetical merger could materialize.

Therefore, I chose to take action.

Having made several trips to Hawaii in recent years, I decided it was time to consider adding a Hawaiian Airlines credit card to my collection. I rummaged through my work desk drawer to find the card applications I had saved from flight attendants.

I thought the saying "in for a penny, in for a pound" was fitting, so I applied for both the personal and business versions of the Hawaiian Airlines cards. This way, I could fully capitalize on the sign-up bonuses that might disappear (or at least change) if the loyalty programs ultimately merged.

In my situation, this translated to an offer of 65,000 HawaiianMiles after making a purchase within 90 days for the Hawaiian Airlines® World Elite Mastercard®. The other offer was for up to 60,000 HawaiianMiles after spending $2,000 and using an employee card within the first 90 days for the Hawaiian Airlines® World Elite Business Mastercard®.

The details for the Hawaiian Airlines® World Elite Mastercard® and the Hawaiian Airlines® World Elite Business Mastercard® have been gathered independently by Dinogo. The card information on this page has not been reviewed or endorsed by the card issuer.

You don’t need a large business for this strategy to be effective. Even a small business, like an eBay store, qualifies you to apply for a business credit card using your name as the business and your social security number instead of an employer identification number.

While the personal card isn't ideal for everyday spending, it offers 3 miles for every dollar spent on Hawaiian Airlines purchases and 2 miles per dollar on groceries, gas, and dining. It has a $99 annual fee, but I think that's a small cost for all those miles.

The business version of the card features similar earning rates. Like the personal card, it grants 3 miles per dollar spent on Hawaiian Airlines purchases and 2 miles per dollar on groceries, gas, and dining. It also carries a $99 fee, which is not waived for the first year.

As is often the case with credit card applications, after submitting my requests for the two cards, I found out I wasn't immediately approved. Both online applications displayed messages saying, "Thank you for your interest. Your application is under review."

Fortunately, I received the first of two phone calls from Barclays just a few minutes later. After answering a few questions about my application, I was verbally approved for the new account over the phone. A similar process occurred shortly after for the other application.

Within a week, my two shiny new Hawaiian Airlines credit cards arrived in my mailbox, ready for use.

TPG's managing editor for credit cards, Matt Moffitt, also took this leap, applying for both the personal and business cards on the same day in August 2024. He was promptly approved for the personal card with a $20,000 credit limit, while his business card application was labeled as 'pending.'

He then contacted the Barclays reconsideration line and learned that he needed to transfer some credit from the personal card to the business card for approval, splitting the $20,000 limit evenly between the two. Like me, Matt received both cards in the mail a week later.

From these two credit cards, I accrued 138,000 HawaiianMiles. If they eventually convert at a 1:1 rate to Mileage Plan miles, as I hope, I should have more than enough miles for a round-trip business-class flight like the one I took to Taipei, Taiwan, with Starlux last year. That trip cost me only 120,000 Mileage Plan miles back then, although the award rates have since increased.

Even if the miles don’t convert, whether due to the merger not being approved or an unfavorable conversion rate, I still have many ways to utilize my HawaiianMiles. One redemption I'm considering is a business-class seat on a Hawaiian Airlines flight from New York's John F. Kennedy International Airport (JFK) to Daniel K. Inouye International Airport (HNL) in Honolulu.

I've spotted seats available for as little as 80,000 miles one way, though I typically find one-way first-class awards for 130,000 miles for the long nonstop journey from New York to Honolulu. The ticket's cash price exceeds $2000. I’ll certainly be able to utilize my HawaiianMiles ... even if they don’t convert to Alaska.

I’m eager to see how the proposed merger and the HawaiianMiles and Mileage Plan programs unfold. There's been significant discussion in the Dinogo newsroom about the potential impacts on the loyalty program. While Alaska hasn't publicly disclosed how Hawaiian rewards will be valued, The Beat of Hawaii reported that Alaska indicated in an email the currency would convert to Alaska Mileage Plan at a 1:1 ratio. Some of my colleagues at TPG are doubtful about that conversion rate, but I believe it’s likely to happen.

For context, when Alaska took over Virgin America in 2016, the previous program's miles converted to Alaska at a rate of 1.3 Mileage Plan miles for each Virgin America Elevate point.

In the meantime, I’ll relish having another reserve of miles for future use.