Frequent Miler on the Air - How do you decide whether to buy flights with cash or miles? | Question of the Week Ep10 | 7-26-26

Episode Date: July 26, 2026

How do you decide whether to buy flights with cash or miles? Follower Owen asked this question recently, saying:"On the podcast you guys often say that you rarely book flights with cash. I find that, especially when booking domestic flights, I often can’t get amazing value from my points (let’s say <1.5cpp). As a result, I tend to hoard my points for those big outsized value redemptions (international business class, Park Hyatt stays, etc.) so I end up booking the flight with cash. How do you think about these situations, especially when you have less flexibility around dates? (Let’s say you’re traveling for an event, or just traveling during peak season). How much do you value the extra flexibility that comes with booking with points? At what point do you decide you have plenty of points so redeeming for lower value isn’t the end of the world?"We’ve been answering a reader or listener question at the end of each Frequent Miler on the Air podcast episode. Now, we’ve turned the question of the week into its own weekly episode. Tune in every Sunday at 5pm for our Question of the Week podcast. And if you have your own question you’d like to submit, you can send it to [e-mail] in this episode:Frequent Miler Beginner's Guidehttps://frequentmiler.com/start-here/Check out all of our other travel podcasts from around the worldThis podcast is part of Voyascape, a podcast network that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsored content on any of our shows you can find out more at the link below.Voyascape Podcast Network

This is a Voyescape podcast. You can find all of our travel podcasts from around the world at voyescape.com. How do you decide whether to buy flights with cash or miles? This week's question comes from Owen, who asks us, when do you pay cash for flights? On the podcast, you guys often say that you rarely book flights with cash. I find that especially when booking domestic flights, I often can't get amazing value from my points, let's say less than one and a half cents per point. As a result, I tend to hoard my points for those big outsized value redemptions, international business class, park high its days, et cetera, so I end up booking the flight with cash.

How do you think about these situations, especially when you have less flexibility around dates? Let's say you're traveling for an event or just traveling during peak season. How much do you value the extra flexibility that comes with booking points? At what point do you decide you have plenty of points, so redeeming for lower value isn't the end of the world. This is a great question that comes in from time to time. And a lot of people, I think, struggle with deciding when do I use my cash or when do I use my points. So, I mean, what are some of the things that you consider? Yeah, I think it's a great question. And it's, and the answer, unfortunately, is more of an art form, I think, than a formula. You know, and I think a lot of it gets to that last part where he said, at what, where he said,

at what point do you decide you have plenty of points for redeeming, so that redeeming for lower value isn't the end of the world. That's such an important consideration because, yeah, people that have a small balance of points that is only enough points to maybe get really good value for one trip a year, let's say, then the answer is pretty easy. Like, save your points for that, you know, one big trip where you're hoping to get really good value. But for those who have many hundreds of thousands, maybe millions of points around different currencies, as I think Nick and I both do, you know, it's a little different. Then the question's more about we want to make sure we're getting good value for our points, but it's not essential to like,

you know, hold on to to those points for that one big thing. So I think it really does change your perspective. I will say that before we get into sort of specific answers here, that I think it's an oversimplification to say that we rarely book with cash, or at least that I do, that there are plenty of situations where I'll book with cash, like I want to use a Delta companion certificate, and the only way to use that is to book the primary with cash. Or I have some kind of, you know, credit card rebate for booking airfare, or I've got flight credits, those kind of things. So there's a lot of things that come up where it's like where I do book with cash,

even regardless. But anyway, so those are some sort of big picture thoughts from my end. But Nick, maybe you have some more specific things you want to cover. Yeah. And by contrast, by the way, it's true that I rarely book flights with cash. There are some instances like Greg said, and we'll get back to that in a second. but I don't book very many flights with cash. So that is true for me. So how do we think about it? Because I think Greg's point about the number of points you have, having a lot of influence on this decision is really relevant for us.

So I start with the reasonable redemption values. We have a reasonable redemption values page. If you just Google frequent miler, reasonable redemption values, you'll find it. And that provides what we found to be reasonable redemption value for all of the various. airline and hotel programs, and then our reasonable redemption value for transferable currencies. Now, the airline values in most cases are based on real data that we've been able to gather from points path in terms of the value that people see when they're searching for flights, you know, real world data based on millions of data points. So it's a huge set of data. So those reasonable redemption values for airlines, for the most part anyway, are pretty, I would say, almost ironclad in terms of what you can reasonably expect to get.

So that's my first reference point. It's the average across huge datasets of searches that's on average. So you can do much better. You could also do worse. But it's a really good solid number to start with. Right. So my first, my first sort of litmus test is how close is it to the reasonable redemption value?

Am I around there? Because if I'm far lower than that, that's a problem. If I'm better than that, it's a pretty easy. okay, well, that seems like a good use of miles. If I'm close, since I have a lot of miles, if I'm within, you know, if I'm a tenth of a cent off of reasonable redemption value, I don't sweat that. That's close enough for me. Now, to Greg's point, the next thing I have to consider is how flush am I with miles? You know, if I've got a million miles in an airline program, I'm much more likely to use them at that tenth of a cent less than reasonable redemption value or whatever

the case may be, a little below reasonable redemption value. If I only have 100,000 miles, totally different story. I'm much more likely to use cash to preserve the miles. So that's a big consideration, I think, for anybody in this hobby is to say, okay, well, do I have tons and tons? Because if I get millions of miles, I need to look for reasons to use those miles. You know, I think that a key point for me anyway is the miles rarely appreciate in value. You know, they're not often going to go up in value over time. Cash is. So if I've got a million miles to use, then I'm going to prioritize using those miles first

and keeping cash in the bank or investments or whatever the case may be, rather than taking money out to use for airline tickets and preserving miles for the future. But again, if you are in that mode where you're like, no, I need to preserve so that I can get that one big trip. per year. I know I'm going to use them to a better value in the near term, then obviously that calculation is going to be different for you. I consider how easy is it to replenish the miles? Like, if I'm going to earn these miles back well before I'm going to need them again, then I, again, I don't sweat the small differences from reasonable redemption value nearly as much as I would for an airline currency that's really hard to earn. And so, you know, to put an

example to that, I guess. Like, I earn a lot of membership rewards points every year. So Air France, KLM miles are really easy to replace, right? Because I can, well, I said membership rewards, but I earn lots of transferable currencies and they all transferred Air France, KLM flying blue, Capital One and Amex and Chase and whatever. So I don't hesitate much on using Air France KLM flying blue miles when a good opportunity arises. It's easy to get more of those. So it's not hard for me to part with those. Alaska Miles, on the other hand, And a little bit more difficult. Now, you can transfer from built, but it's hard to earn a ton of Alaska miles for the most part.

So I'm more careful with how I redeem those miles because they're harder to replenish. So I think that's, I don't know, that's an important component for me. Do you think of that? Yeah, I mean, all of those things are definitely factors. You know, the number of points you have, let me give an example of where it comes up in the real world is, let's say you're going to book a Delta flight that's available to, book through partners. I have close to a million Virgin points, and at the moment, not that many Air France-K-L-L-M Flying Blue points. So sometimes Air France Flying Blue has cheaper prices to book Delta flights than

Virgin Atlantic, but because I'm so flush with Virgin Atlantic points, I'm often tempted to book through them instead. And if it's for a domestic Delta flight, that there's an additional reason, which is the flexibility of canceling cheaply. So Virgin Atlantic, and this is just something we know, we've had posts about this in the past, that when you book a Delta flight, like a domestic Delta flight with Virgin Atlantic points where the only taxes and fees are the $5.60 each way, then you cancel. Even though Virgin Atlantic has a higher cancellation penalty on awards, they only charge you five dollars and 60 cents in other words you get back your miles and they keep the five

and sixty cents that you already spent I don't think that's true with flying blue so I think I would have to pay the full what is it 70 or 80 euros yeah and so that's another big consideration so all of those things and this is why I said as an art form before all those things are all swirling through my head when I'm looking to book one little delta flight absolutely totally makes sense yeah and I consider what's my my next most valuable use for those miles. And so Virgin Atlantic is a great example where, you know, I don't, I don't fly Virgin Atlantic very often. So if I had a lot of Virgin Atlantic miles, for me, if I were looking at a domestic delta flight, I'd say, well, my next best use of Virgin Atlantic miles is

probably I would use them to fly Air France, KLM flying blue because they have decent business class pricing to and from Europe. And so, okay, if I, that's my next best use case for those miles. Am I likely to do that sometime in the near term or not very likely to do that in the near term because if I'm planning a trip like for a couple of months from now where I think I might use those miles to really good value in a situation like that then I'm much more likely to hang on to the miles but if they're going to sit there unused for a while in the account this is probably the case or at least sounds like Greg has found to be the case for him then I'd probably be much more likely to use those so you do have to kind of consider what that next best use case is and if you're looking at domestic airline miles

I'm looking at my United Miles and my next best use case is probably for another domestic trip and maybe I'll get a couple tenths of a cent more in value. I'd probably prioritize using those now and say, you know, maybe I'll use them to slightly better value, but probably not far higher value. So I'm not going to sweat that and I'd use them now. Now, if by contrast, I'm like, well, actually, I usually get really good value out of my United Miles and this is kind of a below average redemption, well, then I'd probably be more hesitant to use them in that case. So really, you've got to, I just consider what your next best redemption is likely to be and how likely that is to happen. Jamie writes in, love the show, but I have no idea what you're talking about. Please help.

That's true. Well, this can be confusing. And luckily for you, Jamie, we have a beginner's guide that can help. You want to go to frequentmiler.com slash start here to check out our full beginner's guide. Flexibility, though. This is something that Owen mentioned in the question that is going to vary from person to person as to how much it matters. But for me, this is pretty important because points bookings are often flexible. Like Greg mentioned, those virgin domestic flights, Delta really, domestic flights booked with virgin points are pretty flexible. You just cost you $5.60 to cancel with a lot of the U.S.-based programs.

cancellations are free. And so that is a huge benefit for me. And oftentimes, I do value that quite significantly. I just the other day was booking a, I don't know, speculative weekend trip to Florida in December. And who knows whether that trip will actually happen. And I was actually about, I have a bunch of Southwest flight credits that I've earned over time. And I was about to combine flight credits and use flight credits to buy the return leg of that trip. And then I thought to myself, I was like, you know what? I don't know whether this trip is going to happen. And when I cancel, I'm going to have a flight credit that's going to expire in the near term. And I got to, there's some tricks around making that so that it won't expire.

But, but, like, do I want to jump through all those hoops in December? Do I want to count on those hoops still being there if I need them in December? Or I might end up stuck with a flight credit that's going to expire in, like, three weeks if we don't take that trip. I thought that headache isn't worth it. I'd rather just book with points and. and retain the flexibility there. And so I think that varies, though, from trip to trip. You know, if there's like a wedding, an important wedding that I'm traveling for,

where I feel like I'm not going to cancel that unless one of us ends up in the hospital, well, then I probably would be more likely to use cash. I'm somewhat ironically, I'm somewhat more likely to use cash for nearer term trips, which tend to be more expensive and historically have been the opportunities to get good value out of your points, actually, nearer term stuff. But there are enough times when I have booked with cash for pretty close in stuff where I'm pretty sure I'm going to go. And I'm less likely to use cash, actually, for stuff that's like way far in the future unless it's for something really important. But I think you probably, you operate differently on this, I think, maybe.

Yeah, well, you know, part of the reason things are different for me is because I'm at a Delta hub. And between my wife and I, we have lots of Delta miles. And Delta, for the most part, their miles are worth sort of a fixed amount that's a little bit over a penny each. And so, you know, even though it's possible sometimes to get significantly more than that, I am totally fine just using my Delta miles to get exactly that. And so I just treat it as like in another way of using cash that is a little more flexible. of all, you know, Delta allows you to cancel cash bookings as well, but you get back a flight credit instead of the original, you know, purchase approach. And so with Miles, it's a little more freely cancelable in that. You get back the miles and whatever taxes you paid, go back to your

credit card. So it truly is completely free to cancel as long as you don't book basic economy. And yeah, so again, unless I'm, you know, doing something like using companions or where you can't use miles, I'm perfectly happy to use miles for kind of just the RRV value straight up. You know, that's an interesting point you make there for two separate reasons. First, I'm very similar with our Southwest points. So Southwest Rapid Rewards points are usually worth around 1.3 cents per point. I did recently redeem some for between 1.4 and 1.5, but I don't usually bust out the calculator

with Southwest points because I know that it doesn't vary a lot. It does vary some, but it doesn't vary a lot. And so I know I'm always going to get around there. We've usually got a decent stash of Southwest points on hand. So I'm not super concerned with it. I'm much more likely to value the flexibility of booking with points. So I often don't think hard about it with Southwest. And I'm not going to stress over is at 1.26 cents or 1.32 cents. Forget about that. I'm just going to use the Southwest points most of the time. Interestingly, so we don't travel a ton domestically. We do travel domestically, but not a ton domestically. When we do, it's almost always Southwest, because now we have two companion passes in our household. So it rarely makes sense for us to book

awards through anybody else. We're almost always using fewer Southwest points than what it would cost us for four passengers otherwise. And I do value the flexibility, lot because I have young kids and they get sick and we've had to cancel things now numerous times at the last minute. So I really do value that flexibility. But so an interesting thing you mentioned was if you use cash, it's kind of flexible. It sounds like you're looking at it from the perspective of, well, if I cancel, I'll get a flight credit and I'll use that for a future trip. And so it's kind of similar flexibility-ish. But then you said, as long as you don't book basic economy. And that's something I do value about points, especially with Southwest now. If you're a credit card holder with

Southwest, there's not much disincentive to book the basic fare with points. If you book with points, you can cancel for free and you still get your cardholder seating benefits and checked baggage benefits. The only thing you give up is the ability to change. So you can't change to another fair class without paying a fair difference. So that's the big thing you give up when you book basic with points. When you book basic with cash, it's a different story because if you cancel that, you get a flight credit that expires six months from the day you booked, which means it could be already expired when you go to cancel if you'd book more than six months in advance.

So there's a big advantage there to booking points. Like when I'm booking with Southwest, I'm mostly booking basic tickets these days. And then I want to book it with points and not with cash because points has that additional flexibility that cash doesn't really. Yeah. Yeah. And to be clear with Delta basic economy, the rules aren't different depending on whether you

book with points or cash. So I don't have that luxury that you're describing with Southwest. So that is really compelling. I would definitely do the same if I was in that situation. Yeah, and it varies. And of course, there are times when I book a choice fair with Southwest, to be clear for anybody who's like a Southwest regular out there, because the major benefit of a choice fair is the ability to do a same day change without paying any difference in fair. So there are times when I'll book choice if I think there's a chance we're going to need to change. but if I'm booking the itinerary that I know we want for that day, and I know we're not going to change to another one,

which oftentimes I'm doing these days, then I'm booking the basic with points most of the time. So yeah. So anyway. All right. So what about situations where you have a credit card benefit that lets you get better than a penny per point using your credit card points? So for example,

Bill lets you get 1.25 cents per point. Rove actually isn't even a credit card one. It lets you get, I think, better than a penny per point. You have Chase, which has points boosts, which if they're available for the flight you want, you could get up to two cents per point depending on the situation. So what about those kind of thing? Oh, and I should mention also business platinum card, where you could get a 35% rebate on a flight booked with your preferred airline,

which leads to a point value of just over 1.5 cents per point each. Do you sort of book with cash that way by using points for cash fares? Not often. I have. When we did, so JetBlue ran the 25 for 25 promotion in 2025. It was at the time it was possible to book a bunch of flights and earn status for 25 years and a whole bunch of points. And so because I didn't want to do that with cash,

I didn't want to dump the cash into that. It would have cost a lot for a family of four. And I had a lot of points on hand, which goes back to our, if you've got millions of points, then you're more likely to accept lower value. I use them in that instance to go after that specific goal because for me, it wasn't just getting one and a half cents per point on the flights. It was getting one and a half cents per point plus the huge mileage rebate that you got, plus the status for 25 years that we've already put to use numerous times already.

So it was a lot of plus plus there. So it was to me more than the one and a half cents per point. Now, I would tell you that I rarely consider doing this because with my transferable points, my goal is usually two cents per point or better. Even though our reasonable redemption value is one and a half cents per point, I travel enough internationally in premium cabins that I tend to target more like two cents per point out of my transferable points for the most part. So I don't usually look for this. I almost never look for it with Chase because most of my Chase points have historically gone to Hyatt. However, that said, I did recently redeem for a hotel booking where I redeemed at 1.65 cents per point through Chase.

It was the edit booking. So through that lens, I guess I should also be looking for flights through there at 1.65 cents per point. For some reason, that's a barrier for me. I don't want to redeem my miles for flights at that cash value, even though I will redeem individual airline miles. Let me restate that. I will redeem individual airline miles for less than 1.65 cents per point. My transferable currency points, I have a hard time parting with them at that value.

That's not really consistent with everything else I've said. I mean, I think that's reasonable because, you know, you can, you know, you're going to have situations where you want to transfer to partners where you're going to. to get way more value than that, right? And so you like to keep them in that in the form that they're in unless you're going to get that bigger value. I think that makes sense. I have a hard time with that, too. You know, I still have, I'm grandfathered into the Chase 1.5 cents per point for a while. I can't remember when that ends sometime in 2027, I think. And I have a hard time pulling the trigger on that, on booking flights and getting 1.5 cents per point value.

Sometimes I've occasionally done the thing with the business platinum where you get the 1.5 for a cents per point value, but partly because historically I've had less uses for the Amex points than I've had for the chase points, but also because sometimes with Amex, sometimes they have these insider fairs that go along that that are only available if you book with points. They're better than the fair is found elsewhere. And you get that points rebate that that gives you the good value. So that combination is really nice. It is.

Anyway, a long way of saying, you know, I don't often do the booking with cash or with points that are like cash, but every now and then something comes across where it works out. I think it's worth mentioning since we brought that up that there are some downsides to booking through the credit card portal in terms of your flexibility and if things go wrong and you need to make some sort of a change. You can't book or you can't deal directly with the airline rather. And so it adds some barriers that to me like that's a cost. And so that detracts some from the value. And there's not an exact cash amount that I can assign to that. It doesn't feel like full cash value in the same way that using cash.

to book directly through an airline would. Now, all that said, if I were spending more money on cash bookings, I would probably be considering using points more often. I'm not using cash very often. So I'm not often considering using the points. I wouldn't want to be dumping many thousands of dollars into flights. If I were sitting on a million points that I could use at one and a half cents per point, I probably wouldn't want to spend five or $6,000 out of pocket on flight.

I'd probably be more likely to be using my points at one and a half cents per point. I'm not usually spending that much on flights in terms of like cash bookings over the course of a year. So I'm not usually feeling much pressure to use points at one and a half cents per point. But like I said before, I mean, cash can increase in value over time and points rarely do. So I wouldn't fault someone for using points at one and a half cents per point with any of those or better with any of those types of methods that exist. This episode was produced and edited by Carrie Yoder, music by Annie Yoder. If you've enjoyed what you've heard today and you'd like to get more of this in your email inbox each day or each week, go to frequentmiler.com slash subscribe to join our email list.

Follow us on all the various social media. Join our Frequent Myler Insiders Facebook group. And wherever you're watching or listening, don't forget to like this or give it a thumbs up. If you have a question that you'd like to be considered for a future question of the week or a piece of feedback that you'd like to be considered for our giant mailbag. You can send that to? Send it to mailbag at Frequentmiler.com. Hi, I'm Mike Siegel comedian and since 2011 host of the Travel Tales podcast.

When I'm not traveling the world telling jokes for money, I'm traveling for fun out of curiosity and love of new places. And I love talking about travel with other people who share my passion. Whether they're travel experts, influencers, expats, or I'm just catching up with a fun friend. The subject is always my favorite one, travel. So if you love travel and want to listen to other people who love travel, and maybe even laugh or learn a thing or two,

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