Award alerts to the rescue, Hilton flushing value, tracking card coupons and more [Week in Review]

Back in March, I wrote a post about a handful of award bookings I had recently (as of late February or early March 2025) made with Alaska miles. One of the trips mentioned in that post was business class for four passengers from Tahiti to the west coast of the US. In that post, I noted that while I had booked a hotel and those flights back to the US from Tahiti, I didn’t yet have a way to get to Tahiti. Still, I didn’t let that stop me from booking the parts of the trip that were available at the time!

I also mentioned in that post that I had set award alerts (in early March 2025) to search for availability to get to Tahiti. I had come up dry in my efforts to find a good way to Tahiti for more than six months. Then, a few days ago, BOOM: I got an award alert from Award Tool that four seats had opened in business class on a near-perfect day to get to Tahiti! I sprinted upstairs to the computer to see that the flights were still available and book them. It was the only day in the entire month in which we plan to travel that had availability even for one passenger in business class at 60,000 miles, and, lucky for us, they had four seats on that single day! Of course, I booked it.

Since that flight would have us arriving a few days earlier than we’d planned, I got excited about the chance to check out Moorea, which we’d missed on a previous trip. The problem is that the Hilton Moorea did not have any standard room award availability. I went to Max My Point and set an award alert for the Hilton Moorea. Sure enough, around 1:20am a couple of nights ago, I got the alert that standard awards were available for a couple of the days we needed! By 1:25am, I had booked a room. I think we’ll actually need a second room if we want to stay there, which hasn’t yet become available. However, I am confident that my award alerts are set and will catch the availability I need in time for the trip!

All that is to say that award alert tools have really changed the game for me in terms of trip planning. I used to stress about finding awards like those, compulsively searching throughout the day (day after day). I still do some of that (award travel is both my job and my hobby), but I spend far less time searching than I did in the past thanks to the ability to “set it and forget it” with award alerts. They have really reduced my trip-planning stress and increased my confidence in booking a partial trip with the knowledge that I’ll probably snag the rest of it later. Check out more in our comparison of flight award search tools and hotel award search tools.

This week on the Frequent Miler blog…

Analyzing Hilton’s spiraling devaluations

In short order, Hilton has gone from dark horse darling of the points and miles world to a cautionary tale of the reasons you don’t want your primary hotel program to offer dynamically-priced awards. In this post, Greg analyzes why he thinks the Hilton/SLH partnership is spiraling out of control. Unfortunately, this epidemic is spreading beyond SLH properties to many of the other highly desirable Hilton properties. I just can’t see collecting 250,000 Hilton points to use them on a single night, so I am effectively priced out of the top-tier properties except with free night certificates. I continue to be excited about collecting those for use at top-tier properties, and I think there is still value to be had at the lower and mid-tier of Hilton, but they have gone from having the most compelling high-end in award travel to completely discouraging members from even collecting points thanks to out-of-reach pricing at top-end destinations.

Fun with Hilton math: Cash & Points Edition

Thanks to things spiraling out of control at the top end, you might someday find yourself short of the points you need to make an award reservation without topping off with some cash. Most readers know that Hilton offers dynamic award pricing, where the points cost of a particular hotel varies with the cash cost. It logically follows then that the value you get per point can vary. Our post analyzing what Hilton points are worth explores the range and frequency with which you’ll find outliers, but I hadn’t previously considered the effect this all has on what Hilton calls “Points & Money” bookings. If you find yourself running out of Hilton points and considering a Points & Money reservation, you’ll want to use this option on a lower-value redemption rather than a higher-value one. If you do get about average value for most of your Hilton points, a commenter points out a play that I intended to feature in the future: using Points & Money to use up some quarterly Hilton credits, essentially “buying back” your own Hilton points with your credit card credits.

Elite status via credit card spend: AA vs Delta vs United vs Alaska vs JetBlue vs Frontier

Greg has updated this post about spending toward elite status with American, Delta, Alaska, JetBlue, and Frontier to now account for the Alaska Summit Visa card. That card is a bit of a long-play game at the time being, since the 10,000 status points are an anniversary bonus. Get the card now to get 10,000 status points next year. I do have some long-distance Alaska travel plans for next year that would get me about halfway to silver, so just getting the Summit card would basically get me there. Add in big spend on that card and Alaska could be a great option for spending your way to oneworld elite status.

Intercontinental for fewer miles than domestic travel: Stretching Virgin Atlantic and Avianca Lifemiles dynamic pricing

In my 100K Vacay planning, I’ve been consistently surprised by the great options available using Virgin Atlantic miles or Avianca Lifemiles for economy class travel. Flying all the way to India for just 12,000 miles and ~$240 or to Santiago for about the same number of miles and far less yet in taxes are but two examples of the deals I’ve run across. Premium economy to London for 10,500 miles and about $240 in taxes is another sweet spot worth exploring. I still wouldn’t speculatively transfer points to either program since dynamic pricing means that any of these awards could drastically increase in price at any time, but you can definitely score some deals with both programs right now.

What are you spending on credit card annual fees? | Ask Us Anything Ep79 | 9-3-25

On the first Wednesday of every month, the Frequent Miler team gets together live on Youtube at 9pm Eastern on the first Wednesday of every month to answer your questions about points and miles. If you missed the September session, you can catch the replay here. As a reminder, the October 1st Ask Us Anything will mark Greg’s return from the benchmark trip and will be the official kick-off for the 100K Vacay travel period for Tim, Stephen, and me.

Our favorite travel gear | Frequent Miler on the Air Ep323 | 9-12-25

We field questions from time to time about our favorite travel gear or how we pack for our challenge trips, so this week on Frequent Miler on the Air, Greg and I took up a full episode to talk about the things we never leave home without. From things we’ve mentioned numerous times before to things you might not think to have in your bag, this week we share all the stuff we have come to love and pack again and again.

Coupon Book Tracker 1.0

In an effort to organize my own coupon credits, I created a coupon book tracker spreadsheet. I was primarily interested in making sure I have used Platinum card benefits like my Saks credit and Fine Hotels & Resorts credits across all of our household Platinum cards, but then I expanded to prepare for when we soon get access to Sapphire Reserve credits and to track some other Amex coupon benefits as well. This is only version 1.0 of the sheet because I wanted to get organized now rather than put it off for later, but I will be updating and expanding the sheet over time.

Citi locking accounts for many Strata Elite customers, requesting tax transcripts

We occasionally see some card issuers lock the accounts of some cardholders to verify that those cardholders are financially capable of supporting their spend, though that happens more rarely than one might expect. Citi has instituted what might be the broadest financial review we’ve ever seen, locking accounts and requesting tax transcripts from many, many folks who opened Strata Elite cards in the first month after the card launch. Making matters worse, they apparently insist on snail mail to send a form and return it to their PO Box, which means that some folks who are traveling may not be able to complete that in time to avoid shutdown. This does not appear to be affecting those who opened accounts in the last two or three weeks, but it is a major headache for many others.

Avios transfers are back between British Airways, Iberia & Aer Lingus

We had recently reported that transfers between British Airways and Iberia, and Aer Lingus were down. This post explains that they are (thankfully) back again and with a different format that will probably be good news for most.

How to pay taxes via credit card, 2025 edition

Third-quarter estimated tax payments are coming due this week, which presents an opportunity to pick up a new intro bonus or perhaps meet a big spend bonus, depending on your situation. This post explains your options for paying via credit card, why you might want to, and which cards you might want to consider using.

That’s it for this week at Frequent Miler. Check out this week’s last chance deals to make sure you catch them before they’re gone.

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