One of the ways in which my travel habits have changed significantly since becoming entrenched in miles and points is the flexible way I look at plans, even those plans that seem solidified. Even when a trip is “set”, I can’t really resist keeping an eye out for a better opportunity, which always keeps my plans in flux.
As I type this post, I am heading to the airport for a European Christmas Markets trip that was almost entirely planned 9 months ago. In fact, this trip has had very little flexibility compared to most we take, with 2/3 of the trip including either a completely nonrefundable hotel, or a hotel booked at a rate so far below current rates as to make it impractical to reschedule. Still, I couldn’t resist keeping an eye out for a “better” flight option on the front end of the trip.
Award search tools make that so much easier these days, and I really lucked out when Award Tool helped me find availability on SAS, which presented the perfect opportunity to use just 20% of my Million Mile Madness haul to fly 5 of us in business class to Europe. People sometimes ask me how much time I spend booking a particular trip, but the truth is that I don’t really stop booking a trip. Even as we head to the airport, I’m still watching the tail end of the trip for a better hotel, and I have some alerts set with MaxMyPoint in case a hotel I like more opens up closer to check-in day.
And while that might seem “crazy” to some extent (and maybe you’re right), it creates an opportunity to stretch your miles and points a bit further. In this specific instance, we preserved some more broadly useful points saved a net 100K points. One or two of those pivots a year can really be worthwhile. Do you need to obsessively search for a better deal? Not at all. With Black Friday deals on, now is the time to pick an award search tool to test-drive at a discount. It is hard to recommend one tool as I use several myself, but better to pick one to try this year while you can get it for less (I’d probably start with PointsYeah or Award Tool if you’re newer to the hobby or Seats.aero if you’re more award-booking-experienced). When I say that these search tools have changed the game, it isn’t an overstatement: they save me eons of time each year and make the wild travels we enjoy more easily achievable.
On the blog this week, we are covering the best of Black Friday and Cyber Monday deals, we point you to the portals that can stack for even better-than-advertised deals, and we ponder which hotel points are the most powerful.
All that and more in this week in review.
This week on the Frequent Miler blog…
Black Friday / Cyber Monday deals, 2025
It’s deal-hunting time! To a certain extent, Black Friday and Cyber Monday are a lot of hype, but if you cut through the noise, you can sometimes score a terrific deal. That is particularly true with shopping portal offers — early on Friday morning, I found 90% back at Kiehl’s via Capital One Shopping, along with 70% back on Serta mattresses, 80% back on Valentino Beauty, 40% back on Saks Off Fifth Ave, and more. If you’re able to stack a great portal rate with a solid deal, you can do really well in the right situation. In this post, we’re keeping a list of curated travel, gift card, and merchandise deals for Black Friday and Cyber Monday, and we’ll try to continue adding to it through the next few days.
Shopping Portal Signup Bonuses
One of the best ways to play a holiday shopping stack is to earn a new portal welcome offer along with an elevated rate of return. Also, don’t forget to make sure that your friends and family are stacking deals, too — at the very least, it is usually worth referring your Player 2 for every portal so you can stack a referral bonus and new account bonus along with the cash back or miles. This post has a list of some of the best portal offers for new customers.
Super Stacking Stories | Frequent Miler on the Air Ep334 | 11-28-25
On this week’s Frequent Miler on the Air, Greg and I start out with a “Wea Culpa” for some errors on last week’s show, we marvel at how Etihad has outdone itself with an even worse cancellation policy for award flights, and we reminisce about some great stacks. I can’t emphasize enough the importance of learning about what has worked in the past, as it is the easiest way to recognize what might work in the future.
A quick pivot to save miles (and money)
Speaking of using the past to recognize the scent of opportunity….
Earlier this week, I made a late-game switch of plans to take advantage of a slamming deal using my SAS miles (200,000 points for 3 adults + 2 kids in business class to Europe!). That meant needing to pay to cancel my original Aeroplan booking, which I knew would not be free. However, I remembered a (now long dead) trick that Greg had written about a few years ago, whereby it used to be possible to book a Flexible award and later change it to a “lowest” award on the same flights to save miles while maintaining flexibility. I wondered to myself whether that now-dead trick might work in reverse. In other words, I had a “lowest” award booked: rather than paying the (higher) cancellation fee to get my miles back, could I pay the (lower) fee to first change to a Flexible award, and then cancel for free, saving big over the cost of straight up cancellation? I almost made a silly mistake in the process, but the only reason I even thought of this and ended up saving a bundle is that I knew about that similar trick that used to work.
My Hyatt premium card wishlist
Greg wrote a wishlist for the coming-sometime-soon Hyatt premium credit card. I’m not sure how I feel about his wishes. In large part, that is because I am not sure what I would want from a premium Hyatt credit card. I don’t necessarily disagree with Greg’s takes here, I’m just not sure I’d be willing to pay $395 (or $495 or $595 or more) for a card that checks off the boxes on his wish list. I think that my wishlist for the card would include an annual Ultimate Free Night Award (i.e. usable at any category) and the ability to earn an additional Ultimate Free Night Award through spend, so long as that spend also earns elite nights at about the same rate as the business credit card. I don’t think it makes sense to reduce the path to status too far, and if they aren’t going to make Mr. & Mrs. Smith properties follow the award chart, I don’t really care about maing the free night certificates work at Mr. & Mrs Smtih, I the st want to be able to use a certificate for category 8 and the all-inclusive properties and the chance to spend toward a second one at a reasonable rate of return.
Which transferable credit card points are most valuable for lodging?
If you haven’t yet read Tim’s post about which credit card points are, on average, most valuable for lodging, try to make a guess before you click on the headline above. The results of his analysis are certainly both interesting and provocative. Are you locked in with the best there is, or sleeping on a set of points that you should be collecting? This post is well worth a read — even if the nuance of tenths or hundredths of a cent per point doesn’t appeal to you in the same way it does to us, the takeaways here are interesting to keep in mind.
Transferring points to hotels. Has Citi eclipsed Chase and Bilt? | Coffee Break Ep79 | 11-25-25
Citi has gone from something of an afterthought when it comes to booking hotels with points to a serious contender, offering a number of solid-value options that you won’t find through “the usual suspects”. Does that put Citi in the lead, or should it still be a supplement to a well-rounded strategy? Greg and I discuss the ins and outs of Citi’s hotel partners on Coffee Break.
That’s it for this week at Frequent Miler. Keep an eye on this week’s last chance deals to be sure you grab those expiring at the end of the month.
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