How I Used Amex Points to Book American Airlines Flights

My New Favorite Sweet Spot: Booking American Airlines Flights with Amex Points (Yes, Really!)

I’m heading to the Disneyland Half Marathon weekend with a group of girlfriends, and you know I wasn’t about to pay out-of-pocket for flights if I could help it. With a little research (and a lot of points strategy), I figured out a way to book all of our round-trip tickets using points—even though we’re flying American Airlines, which typically doesn’t partner directly with Amex.

Here’s the kicker: I was able to cover 3 round-trip flights from Dallas to Orange County for just 45,000 Amex points total—that’s 15,000 points per person, round-trip.

If you’ve ever struggled to use Amex points for AA flights, this sweet spot is going to be your new best friend. Let me walk you through exactly how I did it.

The Sweet Spot Strategy: AMEX ➡ Hawaiian ➡ Alaska ➡ American

Yes, it’s a bit of a three-step shuffle—but trust me, it’s worth every mile.

Step 1: Transfer Amex ➡ Hawaiian Airlines

Amex Membership Rewards points transfer 1:1 to Hawaiian Airlines. The transfer took less than 24 hours for me. Hawaiian miles are a bit under-the-radar, but this is where the opportunity starts.

Step 2: Hawaiian ➡ Alaska Airlines

Here’s the golden trick: Hawaiian Airlines allows you to transfer miles to Alaska Airlines through their “Share Miles” program. There’s a small fee to complete the transfer, but the value you get in return—especially on American Airlines flights—is huge.

Step 3: Book AA Flights on Alaska’s Website

Alaska Airlines and American Airlines are partners, which means you can use Alaska miles to book American Airlines flights directly through AlaskaAir.com. I searched for flights from Dallas (DFW) to Orange County (SNA) and found round-trip options for just 15,000 miles per person.

That means I got 3 round-trip tickets for just 45,000 miles total—all sourced from my Amex points.

Why I Love This Sweet Spot

✅ You can finally use Amex points for American Airlines flights
✅ Insanely good redemption rates (15,000 round-trip is almost unheard of!)
✅ It’s a perfect solution for popular routes and event weekends—like our runDisney girls’ trip!

Things to Know Before You Book

• Award space is limited. Not all American Airlines flights will show up on Alaska’s site, so flexibility is key.

• Hawaiian → Alaska transfers involve a fee and need to be initiated via the Share Miles program (you can transfer to a friend or family member’s Alaska account if needed).

• Plan ahead. Transfers can take some time, so this isn’t a last-minute booking method.

• Ability to Transfer Going Away Soon- In late June the ability to transfer Amex to points to Hawaiian is going away, so you won't be able to do this trick for long.

This strategy was a total win and helped me save hundreds—maybe even over a thousand—dollars on flights for this special girls’ trip. I love finding creative ways to stretch points, especially when it makes travel more accessible and FUN.

If you’re earning Amex Membership Rewards, one card I can’t recommend enough is the American Express Business Platinum Card. It’s been my go-to for years—it racks up points quickly on business expenses, plus gives you perks like 35% points back when booking flights through Amex Travel (select airlines only), premium lounge access, and elite hotel status.

Want help planning your own points-powered adventure?
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📲 And don’t forget to follow my journey on Instagram at @partyof5travels for real-time hacks and behind-the-scenes of this trip.

Let’s keep turning everyday spending into unforgettable experiences—one point at a time.