How and why I used transferrable points for flights to Hawaii

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I just returned a few weeks ago from a vacation in Hawaii, where my daughter, my mom and I were lucky enough to visit both Maui and the Big Island. I’d been eyeing a stay at the Grand Wailea Maui, A Waldorf Astoria Resort for forever, and when I saw award night availability open up for January 2020 I jumped on it.

Thanks to my Hilton Honors Aspire Card from American Express card and the welcome bonus I earned from the Hilton Honors American Express Business Card, I knew our hotel stay would be covered. But flights were a different story.

I live in Missoula, Montana, so finding award flights that don’t involve some sort of crazy routing can be challenging. Because I have a four-year-old in tow, I pay close attention to flight times and layovers.

This is why I’m a huge fan of flexible rewards programs like Chase Ultimate Rewards and Amex Membership Rewards points.

Our five-night stay at the Grand Wailea was even sweeter thanks to the free flights we got using Chase Ultimate Rewards points.

Should you use transferrable points to book flights?

I always keep a stash of flexible rewards for those times that I just can’t seem to find award availability or don’t even want to bother with the hassle of searching for multiple award tickets. In certain instances, I’ve even ended up saving rewards by booking with flexible points.

For this particular trip, I started by doing a quick award search on United Airlines, Delta, and Alaska Airlines. But after looking at cash prices, I quickly realized that my best bet was likely transferrable points because cash prices were reasonable for my travel dates.

Using Chase points

I have a healthy balance of both Chase Ultimate Rewards points and Amex Membership Rewards points but I decided to use Ultimate Rewards because I planned to book basic economy fares. The Amex portal doesn’t display basic economy fares, so it’s impossible to use your Amex Membership Rewards points for those tickets.

Because I’m an Alaska Airlines Visa® Business credit card cardholder, I — along with up to six companions on the same reservation — get to check one bag free of charge. So booking a basic economy fare on Alaska Airlines made sense – I’d save money and still get free checked bags despite the baggage restrictions that would otherwise come with these cheaper tickets. Plus, I get 1.5 cents per point on travel booked through the Chase travel portal for being a Chase Sapphire Reserve® cardholder.

For three round-trip tickets from Missoula to Maui (OGG) and returning from Kona (KOA) to Missoula, I ended up paying 102,720 Chase Ultimate Rewards points and getting free checked bags thanks to having the right travel credit cards. That’s 34,240 points per person — easily over 10,000 points (or miles) less than what I would have paid had I booked through United Airlines, Delta or Alaska Airlines.

Using Amex Membership Rewards points

While I didn’t use Amex Membership Rewards points for this trip, I’ve used them for plenty of other flights to spots like Denver, Santa Barbara, Portugal and Thailand. Whether you use Chase points or Amex points is really a matter of how many points you have and need, and taking the time to compare pricing through each of the portals.

I have The Business Platinum Card® from American Express, for example, and get 35% back on rewards tickets booked with my selected airline. For this reason, it sometimes makes more sense for me to use Amex Membership Rewards points for flights. This is often the case if I’m looking to book a standard economy fare to take advantage of the one carry-on bag allowance.

Do you have a preference when it comes to booking with a particular type of travel rewards? I’d love to hear your thoughts in the comments below!

Featured image by the author.

Meghan Hunter is a contributor to Million Mile Secrets, he covers topics on points and miles, credit cards, airlines, hotels, and general travel.

Editorial Note: We're the Million Mile Secrets team. And we're proud of our content, opinions and analysis, and of our reader's comments. These haven’t been reviewed, approved or endorsed by any of the airlines, hotels, or credit card issuers which we often write about. And that’s just how we like it! :)

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6 months ago

This is a confusing post. So what Airlines did you end up using with the Chase Ultimate Rewards? I’m guessing it’s United. United usually has a free first checked bag anyway. And how did saying Alaska’s free checked bag fit into this scenario? It didn’t. Very confusing article. Just easier to have said you got your tickets using the Chase rewards and nothing else. PERIOD>

6 months ago

off topic, I want to visit a Montana this year. My goal is to visit all 50 states, and I am getting close to my finish line.

I will fly into Bozeman, visit Helena and Missoula.

Any tips ? Foodies to try?

I want to visit Malmstrong AFB too, but that maybe off limits…

Tracey Smith
6 months ago

I’m confused…how did you utilize both the Alaska baggage benefit AND the Chase 1.5x redemption? To get the Alaska benefit you need to book with the Alaska card and to get the 1.5x redemption on Chase, don’t you need to use the Chase card? How did you do both?