A gamble on Alaska miles — why I applied for 2 Hawaiian Airlines cards on the same day

I’m probably one of the most credit card-dependent members of the TPG team. I already have too many for most humans to keep track of, resulting in my need to use spreadsheets to keep up with all my benefits. In fact, at last count, I had more than 20 open cards.

Given how many cards I currently have, I hadn’t really been in the market for another card … until Alaska Airlines announced it planned to buy Hawaiian Airlines back in December 2023.

Alaska says it will continue operating Hawaiian Airlines as a separate brand but will combine Alaska Airlines Mileage Plan and HawaiianMiles into one loyalty program. That opens up the possibility that HawaiianMiles could eventually become valuable Mileage Plan miles … or something similar. That made me want to get some HawaiianMiles banked as soon as possible.

Related: Hawaiian-Alaska Airlines merger: What we know (and want to know) about the future loyalty program

The proposed merger cleared a major milestone in August 2024 when the Department of Justice said it wouldn’t move to block the deal. It still needs the signoff of the Department of Transportation. In a statement, Alaska Airlines wrote the merger, ” … remains subject to the U.S. Department of Transportation (DOT) approving an interim exemption application for the transfer of international route authorities.” The DOT has not given a timetable for its decision.

Still, the DOT approval is widely seen as the lesser of the two major hurdles to approval of the deal.

Either way, I decided on my credit card strategy late last year, well before the regulatory process started.

Admittedly, opening two credit cards based on a hypothetical situation is a very speculative move on my part. However, I place a lot of value in Alaska miles and feel confident there’s enough of a chance of this hypothetical merger becoming a reality.

So, I decided to act.

I’ve taken various trips to Hawaii in recent years, so once I knew I was ready to consider adding a Hawaiian Airlines credit card to my wallet, I turned to my work desk drawer to see what card applications from flight attendants I had stored away.

Related: Why the Alaska-Hawaiian merger could be a win-win for frequent flyers

I decided the old adage “in for a penny, in for a pound” was appropriate here, so I applied for both the personal and business versions of the Hawaiian Airlines cards. That way, I could really maximize the sign-up bonuses that may eventually go away (or, at least, evolve away from their current state) if the loyalty programs did ultimately merge into one.

In my case, that meant an offer for 65,000 HawaiianMiles after making a purchase within 90 days of account opening for the Hawaiian Airlines® World Elite Mastercard®. The other offer was for up to 60,000 HawaiianMiles after spending $2,000 and making a purchase with an employee card within the first 90 days of opening an account for the Hawaiian Airlines® World Elite Business Mastercard®.

The information for the Hawaiian Airlines® World Elite Mastercard® and the Hawaiian Airlines® World Elite Business Mastercard® has been collected independently by The Points Guy. The card details on this page have not been reviewed or provided by the card issuer.

However, you don’t have to have a huge business for this strategy to work. If you have any type of small business — even one as small as an eBay store — you can apply for a business credit card with your name as the business and your social security number instead of an employer identification number.

Related: Do I need a business to get a business credit card?

While the personal card isn’t great for regular spending, it does award 3 miles for every dollar spent on Hawaiian Airlines purchases and 2 miles per dollar spent on groceries, gas and dining. It comes with a $99 fee, but that’s a small price to pay for all those miles, in my opinion.

The business version of the card has similar earning rates. Like the personal card, it provides 3 miles per dollar spent on Hawaiian Airlines purchases and 2 miles per dollar spent on groceries, gas and dining. It, too, comes with a $99 fee, which is not waived the first year.

As can happen with many credit card applications, once I submitted my applications for the two cards, I learned I wasn’t instantly approved. Both online applications were flagged with “Thanks for your interest. Your application is being reviewed” messages.

Luckily, I received the first of two phone calls from Barclays just a few minutes later. Once I answered a few questions about my application, I was given verbal approval for the new account over the phone. The same happened a short time later for the other application.

Within a week, my two brand-new Hawaiian Airlines credit cards arrived in my mailbox, ready to use.

TPG managing editor for credit cards Matt Moffitt has also taken this gamble, applying for the personal and business cards on the same day in August 2024. He was immediately approved for the personal card with a $20,000 credit limit. However, his business card application was marked ‘pending’.

So, he called the Barclays reconsideration line and found out he needed to shift some of the credit from the personal card to the business card to be approved, splitting the $20,000 limit equally between them. Like myself, Matt received both cards in the mail a week later.

From opening these two credit cards, I earned 138,000 HawaiianMiles. If they convert 1:1 to Mileage Plan miles at some point, as I hope they will, I’ll likely have more than enough miles to book a round-trip business-class trip similar to the one I took to Taipei, Taiwan, with Starlux last year. That itinerary only cost me 120,000 Mileage Plan miles at the time, though the award rates have since gone up.

Even if the miles don’t convert, either because the merger isn’t approved or the conversion rate isn’t as favorable as I’m hoping, I can still find plenty of ways to use my HawaiianMiles. One redemption I’ve had my eyes on is a business-class seat on Hawaiian Airlines flight from New York’s John F. Kennedy International Airport (JFK) to Daniel K. Inouye International Airport (HNL) in Honolulu.

I’ve seen seats available for as low as 80,000 miles each way, though I generally can find one-way awards in first-class for 130,000 miles for the long nonstop flight from New York to Honolulu. The cash price for that ticket is more than $2000. I’ll definitely be able to use my HawaiianMiles … even if they don’t convert to Alaska.

I look forward to seeing what happens with the proposed merger and the HawaiianMiles and Mileage Plan programs. There’s been intense debate in The Points Guy newsroom over how the deal will play out for the loyalty program. Though Alaska hasn’t said publicly how Hawaiian rewards currency will be valued, The Beat of Hawaii reported Alaska told them in an email that the currency would be converted to Alaska Mileage Plan at a 1:1 ratio. A few of my colleagues at TPG are skeptical of that conversion rate, but I believe that’s how it will land.

For context, when Alaska acquired Virgin America in 2016, the old program’s miles transferred to Alaska at 1.3 Mileage Plan miles per Virgin America Elevate point.

In the meantime, I’ll enjoy having yet another stockpile of miles for a rainy day.

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