Hawaii Fun: How I Earned ~60,000 Hilton Points by Stacking Hilton Promotions and the Amex Aspire Card

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INSIDER SECRET: When new hotel promotions come out, always register (it’s free and only takes a minute), even if you don’t currently have plans for a trip. You never know when you’ll have an unexpected stay and earn surprise bonus points.

One of the best things about the Hilton Honors loyalty program is how easy it is to earn Hilton points from stays, credit card spending and regular promotions. This is particularly true if you can stack your earnings, as was the case recently on my family’s Hawaii trip.

Because I have the Hilton Honors Aspire Card from American Express, I knew I’d earn 14 points per dollar for incidental charges on our Hilton award stay at the Waldorf Astoria Grand Wailea in Maui. Plus, there was a Hilton promotion at the time (now expired) that would award double base points starting with your second Hilton stay, so my family and I did a sleep-and-park deal at an airport Hilton the night before our departure, partly to ensure the double points would kick in for our charges at the Grand Wailea.

It worked mostly the way it was supposed to, but there were a couple of surprises along the way. All told, between a paid night in Toronto and our expenses at the Grand Wailea, I earned nearly 60,000 Hilton points — enough for another free night at an upscale Hilton hotel or multiple free nights at moderate Hilton hotel brands like Hampton Inn or Home2 Suites.

I’ll show you how stacking Hilton promotions with earnings on an Amex Hilton card like the Amex Hilton Aspire can be very lucrative.

Between stacking Hilton promotions and putting room charges (like luau tickets) from the Grand Wailea on my Amex Hilton Aspire, I earned nearly 60,000 Hilton points. (Photo by Jasmin Baron/Million Mile Secrets)

Stack Hilton Promotions and Amex Hilton Cards to Earn Massive Amounts of Points

Apply Here: Hilton Honors Aspire Card from American Express

Read our review of the Hilton Aspire

Of any of the Amex Hilton credit cards, the Amex Hilton Aspire earns the most Hilton points (14 points per dollar) on purchases charged directly with a property within the Hilton portfolio (including bookings and incidental charges). Plus, it offers automatic Diamond Hilton status, which gets you a 100% bonus on base points earned on spending at Hilton hotels.

While our stay at the Grand Wailea was on points, I knew I would spend at least $1,000 there because I wanted to trigger two Amex Offers and the Hilton Aspire resort credit to save $550 off our room charges.

It’s also got the highest bonus of any of the Hilton cards. You’ll earn 150,000 Hilton points after spending $4,000 on purchases in the first three months of account opening, and the card comes with a free weekend night reward when you first open the account, and every year after on your account anniversary.

In addition to earning a ton of points from using the Aspire card, I’d registered for the Hilton “Go More Get More” promotion (expires September 8, 2019), which awards double base points starting with your second stay. Conveniently, we had planned to do a stay-and-park deal at the DoubleTree by Hilton Toronto Airport on our way to Maui, so by booking a Hilton I’d knock out the first stay and earn double points on our Grand Wailea expenses.

We booked a rate at the DoubleTree Toronto Airport to stay overnight before our departure then leave our car for the duration of our trip — and this triggered the double points promotion for our Grand Wailea stay.

By my calculation I would earn (based on $1,000 in spending at Grand Wailea):

  • 10,000 points: 10 Hilton points per dollar for all members
  • 10,000 points: 100% Diamond bonus
  • 10,000 points: 2x points from Go More Get More promotion
  • 1,000 points: Hilton MyWay benefits offer Diamond guests 1,000 points per stay at Waldorf Astoria hotels
  • 14,000 points: 14 Hilton points per dollar for all members

I expected to earn a total of 45,000 Hilton points (45x points) at the Grand Wailea, which is rather crazy — but it’s not uncommon to see huge earning rates like this when you stack Hilton promotions with credit card earnings. I’ll take it!

In addition, I’d earn more points from our overnight at the DoubleTree Toronto Airport, but I wasn’t as excited about it because there would be no promotional points applied to this stay…or so I thought.

Always, Always Register for Hotel Promotions

I’d completely forgotten about a targeted offer I’d received via email earlier in the spring from Hilton. It offered 3x base points on your next Hilton stay within the promotion period, and luckily I’d signed up.

Now, you’re probably thinking it’s too bad I didn’t apply the 3x to the Grand Wailea stay instead, right? Unfortunately, the 3x promo ended the day before we departed the Grand Wailea, so it would not have kicked in for our stay.

When you encounter a new hotel promotion, take a minute to register — you might get a pleasant surprise down the road.

I’ve learned from experience to always register when you find out about a new hotel promotion, even if you have no plans to stay with that chain. It only takes a minute or two and could end up being very profitable if you have an unexpected stay (as I did). If you get into the habit of always registering, no matter what, you won’t miss out on bonus points if you forget to sign-up later when a last-minute stay lands in your lap.

Thanks to the 3x promo, I earned 12,440 points for one night ($320) DoubleTree Toronto airport (which included parking for the duration of our trip and dinner for five at the hotel restaurant) not counting the 14x from using the Hilton Aspire to pay. Note that you don’t earn Hilton points on taxes, which on this stay came to ~$35. With the 2x Hilton promo at the Grand Wailea, I earned 32,170 points, again, not counting the 14x from the Hilton Aspire.

And between both stays, I earned 14,952 Hilton points (14x points per dollar) from using the Hilton Aspire.

Grand total earned = 59,562 Hilton points.

Earning almost 60,000 Hilton points between a five-night award stay and a single night at an airport hotel is just crazy. Depending on how you like to use Hilton points, you could redeem this for a night at a very nice property like the Hilton Waikoloa Village (60,000 points per night), or stretch it out for four nights (five if you use the fifth night free from having Hilton status) at a 15,000 point per night location like the Hampton Inn Warsaw City Centre, where team member Scott made short work of the complimentary breakfast and free Nutella packets.

I made out like a bandit when I stacked Hilton promotions with the Amex Hilton Aspire — and earned enough points for another night at a fancy Hawaiian resort like the Hilton Waikoloa Village. (Photo courtesy of Hilton)

The math didn’t shake out exactly as I’d hoped with at the Grand Wailea, and I learned something new as well. While I did spend just over $1,000 ($1,039 to be exact, not including $9 in excise taxes), I did not earn 14x points on $300 worth of hotel charges (4,200 points), because they were reimbursed by the two Amex Offers I’d stacked for my stay ($100 and $200 credit respectively). I did, however, earn 14x points on the amounts that were reimbursed by the Hilton Aspire $250 resort credit.

Overall, I ended up earning much more in total because of the 3x promo that had slipped my mind. It was a good reminder to register for any and all hotel promotions, even if you don’t think it’s likely you’ll stay any time soon.

Stack Promotions With Other Hilton Cards

While the Hilton Aspire does earn the highest number of Hilton points per dollar at Hilton hotels, not everyone wants to pay the $450 annual fee (See Rates & Fees). You might instead consider some of the other Hilton cards, all of which are offering increased welcome bonuses through August 28, 2019:

The information for the Hilton Honors Business Card has been collected independently by Million Mile Secrets and has not been reviewed by the card issuer.

Bottom Line

Earning an insane amount of Hilton points isn’t unheard of when you stack Hilton promotions with earning points from credit cards like the Amex Hilton Aspire. I recently earned nearly 60,000 Hilton points from one paid night at an airport hotel and incidental expenses on a five-night award stay at the Waldorf Astoria Grand Wailea. And I’d saved $550 there already by stacking two Amex Offers with the $250 Aspire Hilton Resort credit.

I’d actually forgotten about a 3x targeted Hilton promotion I’d registered for. It was a good reminder to always register for hotel promotions when you see them (don’t count on yourself to remember later) because you just never know when you’ll have a stay that triggers bonus points.

Have you ever been surprised by earning more points than you expected on a trip? Share away in the comments.

To learn more about getting free stays at Hilton hotels, check out our guides:

For the latest tips and tricks on traveling big without spending a fortune, please subscribe to the Million Mile Secrets daily email newsletter.

For the rates and fees of the Hilton Honors Aspire Card from American Express, please click here.

For the rates and fees of the Hilton Surpass Card, please click here.

For the rates and fees of the Hilton Amex Card, please click here.

Jasmin Baron is a contributor to Million Mile Secrets, she 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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