One of the things I love about having a range of miles and points is the sense of confidence it gives me in the ability to figure things out. Yesterday, we made a very tight turn in St. Thomas as part of the JetBlue 25 for 25 promo. In fact, because I hadn’t counted on being ushered landside upon arrival, I hadn’t been prepared for us to need to clear both US customs and airport security in between the flights. We very nearly didn’t make the return flight to San Juan (though, thankfully, we did make it and they did seem to hold the plane a few extra minutes waiting for some other stragglers).
Funny enough, while standing in a long line at airport security, I didn’t feel anxious at all. That’s because I knew that in the worst case scenario — if we missed our flight, couldn’t get another to San Juan and had to stay overnight in St Thomas —Â I knew that we would figure it out. Wyndham and Marriott have a handful of properties in St. Thomas and some of them had award availability. I could always book a cash rate and erase it with Capital One miles if need be. We could use Hotels.com gift cards earned from Capital One Shopping if all else failed. But we might not have even been stuck on the island overnight — American Airlines had some award availability to New York via Miami for 12K miles. United had availability to Newark via Houston for 15K Avianca Lifemiles per passenger. We had lots of options to “fix” things without incurring significant out of pocket expense. And as I learned on Thursday night, changing my Amex-booked JetBlue flights is easier than I’d expected.
Thanks to a healthy stash of miles, points, and free night certificates and a reasonable command of award search tools, I feel far less anxiety about the “What ifs” of travel. Sometimes, it isn’t just the cash value of the points, but the peace of mind that they provide that yields outsized value.
This week on the Frequent Miler blog…
Making a strategic change to pay less for the flight you want
Last week while I was at the Orlando airport waiting to fly home after taking the Dunkin’ flight, I received a text message from a family member asking if they could swing by the house to borrow something. They surely thought I was nuts when I explained that I wasn’t home because I was day-tripping to Orlando, but it turns out that day trip has paid dividends already! Things went sideways right at the beginning of our chase for 25 Dunkin’ airports, but my Mosaic 1 status combined with a little out-of-the-box thinking helped me save $300 — and helped me keep the next couple of dominoes in this trip standing.
The hunt for the best flight award finder
Along with the way that miles and points make a pivot possible, award search tools have greatly improved my confidence in the ability to find that necessary award in a pinch. Beyond that last-minute-award use case, I have to say that award search tools save me an immeasurable amount of time on a regular basis, essentially providing a shortcut to regularly finding great award deals. However, it isn’t as simple as using a single award search tool. As Greg shows in this fantastic post, your results can vary considerably depending on the tool you use — and if you don’t cross-reference results, you may lose out on some great award deals.
Booking JetBlue via Etihad: An exercise in frustration, but great when it works
Among the recent award deals that I’ve found via search tools are JetBlue flights available to Etihad Guest. I had mostly ignored JetBlue for years because they don’t offer much service from my home airport and I had grown to almost completely ignore booking domestic JetBlue awards via partners because I’d never found a single seat available to Qatar on the routes I actually needed to book. I had (incorrectly) assumed that it was mostly tough to find JetBlue flights available to partners. The 25 for 25 promotion has awoken me to the value of using Etihad Guest to book some JetBlue flights — but it isn’t necessarily an easy thing to do.
Hyatt finally has a functional award calendar
Finding great Hyatt awards became much easier this week. The running joke for years has been that “there’s no ‘IT’ in Hyatt”. It seems that Hyatt has heard the call for them to join the 21st century and they now have an award calendar that displays both award pricing and availability for a month at a time. That is a huge time-saver for those with the flexibility to consider travel when availability exists.
Our next all travel card | Frequent Miler on the Air Ep315 | 7-18-25
All this talk about award travel aside, what about paid travel? Given changes in the travel credit card landscape, which card or cards are now the best to use for paid travel? On this week’s Frequent Miler on the Air, Greg and I discuss the options and our preferences.
Citi Strata Elite to launch in-branch Sunday with tiered 100K bonus (more juicy details)
Speaking of travel credit cards, the word on the street is that Citi will be hitting the streets with a brand new ultra-premium travel card of their own, but you’ll need to pound the pavement and get yourself to a branch to get first crack at it. To be clear, there has been no official information from Citi about the Strata Elite, but there seems to be enough credible rumor at this point to think that this card will likely make its grand entrance this weekend.
Frequent Miler origin story – Stephen’s story | Coffee Break Ep63 | 7-15-25 | Podcast
What is one thing that Stephen, Tim, and I all share in common? Our wives are the ones who ultimately convinced us to apply or work at Frequent Miler. Want to know more about how Stephen came to work here and how he developed his mad stacking skills? Check out this week’s Coffee Break as we discuss Stephen’s origin story.
American Airlines 787 Flagship Suite Review: Chicago to London
Greg recently scored a fantastic deal to fly the new American Airlines Flagship business class suite to London. I was very curious to read his review about this new product. As I pretty much expected, the hard product looks very good, though it sounds like service was predictably mediocre. Still, when flying to Europe, my focus has shifted from enjoying a premium experience to trying to get as much sleep as possible on the relatively short overnight flight. The new flagship suite seems like it would be great for that purpose, so I’ll keep this in mind for our next trip across the pond. When returning from Europe, I’d rather fly a carrier that includes great service and/or food with their premium product.
JetBlue TrueBlue Complete Guide (2025)
Tim updated our JetBlue TrueBlue guide this week as JetBlue has been top of mind for many given the current 25 for 25 promotion. This post includes all of the key information you need to know about JetBlue TrueBlue.
Business Platinum pay with points rebate may be posting more quickly
Until the current JetBlue promotion, I hadn’t used the American Express Business Platinum pay with points rebate for quite a while. In the past, my points rebates had taken 4-6 weeks to post to my account, so I was very pleasantly surprised when our recent JetBlue bookings have been posting rebates within 1-2 business days. Many readers in the comments echoed similar experiences for the past several months. That’s a great change that makes this benefit more useful for me since we can use the rebate multiple times now rather than needing to wait a month to get a big chunk of points back later.
That’s it for this week at Frequent Miler. Keep an eye on this week’s last chance deals and make sure to grab them before they’re gone.
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For me, the best reason for always having miles with several airlines (or, as is often the case, transferable miles) is the ability to book an alternate flight in case a possible weather event might interfere with your original plans. Then just cancel as needed.
Such an amazing feeling to not have to worry and just say, its just time we can figure it out.