Travel Hack: How We Pooled Hawaiian, Amex, Alaska Miles for Huge Payoff

If you’re like us, you want to maximize your hard-earned miles and points for Hawaii travel. As a result of the purchase of Hawaiian Airlines by Alaska Airlines, we recently took a deep dive into all related frequent flier options to maximize the outcome.

By pooling HawaiianMiles and American Express points, we leveraged their value and moved them to Alaska’s well-reviewed MileagePlan. The result?

We ended up with a half-million Alaska Airlines Mileage Plan miles, enough to fund multiple trips. Here’s how we did it and how you can do the same.

Keep in mind that you can now purchase Hawaiian Air flights on the Alaska Airlines website, so that having your miles at Alaska doesn’t preclude your using then on Hawaiian.

Why pooling our miles was key to achieving half a million.

We started with a mix of HawaiianMiles, Amex points, and Alaska Airlines miles but faced challenges: Alaska Airlines doesn’t allow you to pool miles between accounts, limiting the flexibility of how miles could be used. However, Hawaiian Airlines still offers pooling for its miles if the transfer recipient holds their credit card, providing an opportunity to combine points from different accounts.

By leveraging this, we were able to create a flexible strategy to transfer points and consolidate everything into one Alaska Airlines account. The goal was to pool as many miles as possible and use them to book multiple Hawaii trips without limitations.

Step 1: Transfer Amex points to HawaiianMiles.

The first step was to transfer our American Express points to HawaiianMiles. While Amex points don’t work directly with Alaska Airlines, they do transfer to Hawaiian Airlines, which became our workaround.

This transfer provided us with a substantial number of HawaiianMiles, which became the foundation of our pooling strategy. This was key since it’s impossible to transfer Amex points directly to Alaska Airlines.

Step 2: Pool HawaiianMiles using the credit card perk.

Once we had a significant number of HawaiianMiles, the next step was to take advantage of Hawaiian Airlines’ unique pooling option. We could pool miles from various family accounts into one by holding a Hawaiian Airlines credit card.

This allowed us to gather miles from multiple sources and consolidate them into a single account. Having a larger balance of HawaiianMiles set us up for the next move: transferring them to Alaska Airlines miles.

Interestingly, we also discovered that you can convert Alaska miles back to HawaiianMiles for additional flexibility. For example, one of us had a significant number of Alaska miles, and the other did not. Bringing those together in one Alaska account required moving them first to Hawaiian, the only choice for pooling miles.

However, there’s an important catch: when transferring miles from Alaska to Hawaiian, they must be transferred to the same person’s account. You cannot transfer them to a family member, business associate, or friend. However, you can do it once the miles are back at Hawaiian. And thereafter they can be moved back to Alaska.

Step 3: Transfer pooled HawaiianMiles to Alaska Airlines (and vice versa).

Once all the miles were at Hawaiian, the final step was to convert all the miles into one Alaska Airlines account. For many people, that provides the best option for two or more people traveling together, allowing you to make one reservation with multiple passengers.

Otherwise, each passenger would have needed to use their miles for a separate reservation, making managing reservations much more challenging. This process created one large pool of miles ready to be redeemed.

By consolidating everything into one place, we ended up with about 500,000 Alaska Airlines miles, which gave us more flexibility to book flights on many airlines and for multiple trips.

The benefits of this Hawaii travel strategy.

This points and miles pooling strategy provided significant advantages:

Maximized flexibility: By pooling miles into one Alaska account, we gained more freedom to book flights on Alaska’s and Hawaiian’s extensive network to and from Hawaii, as well as on partners including American Airlines, and on international carriers.

Multiple trips: Having a large balance of miles in one place meant we could easily fund several trips for multiple passengers, all with one set of miles.

Efficient use of Amex points: Although Amex points don’t directly transfer to Alaska, we found and used a great workaround by using HawaiianMiles as a bridge, making the most out of our points.

Final thoughts: Make the most of your points while you can.

This strategy isn’t just about maximizing miles; it’s about creating flexibility in using them. By pooling miles across both airlines and taking advantage of credit card perks, you can significantly increase the value of your points and miles.

If you’re holding on to HawaiianMiles, Alaska miles, or Amex points, consider a strategy to combine them into one pool. With a little effort, you could end up with a sizable balance ready to fund your next Hawaii vacation.

If you try this travel hack, let us know how it works for you.