Frequent Miler on the Air - Tips for finding impossible awards | Frequent Miler on the Air Ep360 | 5-29-26

Episode Date: May 29, 2026

Today's episode will provide a whole grab bag of tips for how to find those impossible award bookings for your award travel goals.(02:32) - Here's a grab bag of techniques, and keep in mind it's often necessary to use multiple(03:09) - Be flexible!(06:48) - Look towards the end of the booking schedule: use points that can book farther out(08:26) - Positioning flights(20:59) - Programs that reserve more space for their own members(22:22) - Programs that reserve more space for elite members/cardholders(24:17) - Programs that allow more awards for more points(26:47) - Married segment logic awards (e.g. san-lax-tyo available, but lax-tyo not available)(35:07) - Consider programs that allow a stopover(39:04) - Award tool Alerts(41:44) - Paid flightsSubscribe and FollowVisit https://frequentmiler.com/subscribe/ to get updated on in-depth points and miles content like this, and don’t forget to like and follow us on social media.Music Credit – “Ocean Deep” by Annie YoderMentioned 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 atvoyescape.com. If you love award travel, but you've been finding it really difficult to find the awards that you'd like to book, today's show is going to give you a whole bunch of tips about how to find those impossible awards. Frequent Miller on the air starts now. Today's main event, tips for finding impossible awards. I'm recording this from St. Louis. I had a quick weekend trip to St. Louis where I met up with some points and miles enthusiasts. And the question on everybody's mind, it seemed like, was, hey, Greg, I'm trying to find a way to get to Vietnam or to get to Japan or to get to Europe or to get to wherever. I'm not having any luck finding Savor Award. availability, what can I do? And so we'd end up having long conversations about possibilities.

Like, did you try this? Did you try that? Did you try the other thing? And I realized that, you know, all of these things that I was coming up with, while they were specifics for that person's situation, they all fall into different areas of like approaches you can take to look for and find impossible awards. And so for today's show, we're going to, you know, basically go over those techniques on a broader level. I will stress, though, that we are recording this well in advance of actually airing the show. So we may mention things that, you know, as an examples, specific things as examples, that might not be true by the time you listen to this show. But I believe, I firmly believe that all the techniques we talk about will still be true,

but the specific examples we give of like here's exactly how it might unfold might not be the case by the time you listen to this. Yeah, as you've heard us talk about recently a few times probably things change all the time. And so you have to be ready to adapt and adjust. But I think that the travels that Greg and I and the rest of the Frequemiler team have done prove that impossible awards aren't necessarily impossible if you go about things with some of the techniques that we're going to talk about today. If you want to jump ahead to something or you want to come back to it later, don't forget you'll always find the timestamps in the show notes and wherever you're watching or listening. Don't forget to give this a like, a thumbs up, leave us a comment or a review. We always appreciate that. All right, let's get into today's main event.

Main event time. Tips for Finding Impossible Awards. As I said at the outset, we're going to go through a whole bunch of different tips or techniques. You could think of it that way. But keep in mind that for really, really tough to find awards. You may need to use many of the techniques we're going to talk about. It's not like just one technique will be the silver bullet. There are a bunch of techniques to help you find things. And by learning how to do all of them, then you'll be better equipped to finding

those really tough to get flight awards. One of the best ways to find impossible award availability is by being really, really flexible. Yeah, I often tell people that there are kind of three forms of flexibility that are useful when it comes to travel. Cash flexibility, if you have unlimited cash flexibility, just buy what you want. You don't have to worry about it. Of course, if you're listening to this show, that's probably not the situation where you want to be the most flexible.

But I mention it because, I mean, it is relevant, I think, anyway, in terms of the other two. So the other two types of flexibility, I often say, are flexibility with regard to time. Now, that can be the time of year when you travel or the timing of your flight. If you have some time flexibility, whether it's even just the days, the number of days that you have to be able to travel, adding an extra day or two or subtracting a day to find award availability, the more flexible you can be with time, the more you increase your odds of being able to find a flight. If you say, oh, I want to go to Europe in the summertime, it's going to be much easier than saying, I want to go to Paris on June 16th. the more or the less flexible you are on time, the more difficult it is to find awards that fit

whatever your time span is. And then finally, destination flexibility. And that can mean some different things. So by one token, it could be just being flexible to what's available. As a family traveler and someone who's been fortunate to travel to a lot of places with my miles, I'm often much more open to a destination. And I'll say, well, you know what? There's four seats available here. let's go find what's interesting there, rather than planning a trip where I say, okay, we're, we're going to go here no matter what it takes to find that particular, you know, award to get there. Now, you may just want to visit a particular place, and that's fine. What you have to recognize is the less flexible you are on any one of these things, the more

flexible you need to be on other things. So if you know that, you know, you want to go to Europe in June, then you may need to be a little more flexible about, okay, well, where in Europe? Or at least where in Europe am I going to land? If I'm flying to Europe, for instance, it doesn't really matter to me where in Europe I arrive because I can cheaply and easily enough get to just about anywhere, whether I fly into Frankfurt or Paris or, you know, wherever it may be in Europe, I can get wherever it is I'd ultimately like to go. And I generally wouldn't mind stopping a couple of days in Paris or London or wherever it is if I need to stop in between. So the more flexibility you have in that realm, the easier it is to find those

really hard to find awards. Yeah, that is so true. And, you know, I wouldn't even limit it to like Europe as a place where you can easily get from one place or another. Once you get out of the Americas, the ability to find cheap flights and or award flights goes up dramatically. So for example, well, yeah, getting to Asia can be really tough, especially if you're looking for business or first class awards. But once you're there, finding, you know, great flights to fly around Asia tends to be really easy. Yeah, so that's a good example because I've been looking at trying to get to Australia and having a hard time finding availability to Australia. So I just expanded my search. And I said, well, you know what?

Let's look at flying to Japan or flying to Thailand or flying to Malaysia. I'm looking at different places in Asia because I know that it'll be much easier probably for me to find an award from Hong Kong or Tokyo to Australia than it is from Los Angeles to Australia. And that's not to say easy, but it can increase my odds of finding those types of things. So, yeah, I think that's a really good point, really anywhere in the world. Once you get outside of the United States, you're right. Connecting the dots is far easier. Look towards the end of the booking schedule. Now, again, not any one of these techniques will work 100% of the time.

But consider using points that can book further in advance. So most of the U.S.-based carriers allow booking awards about 11 months in advance, but some foreign programs, many foreign programs, offer award booking closer to 12 months in advance. So to give you, for instance, several of the U.S.-based programs offer booking about 330 days in advance. But Air France, KLM, at least as we record this, allows booking 359 days in advance. Or Air Canada Aeroplane offers it 355. days in advance and Avianca 360 and it varies from one airline to another and it may change like Craig said but it's worth taking a look to see which airlines can book farther in advance because that would give you access to that award space before other people trying to book with their

American Airlines miles or United Miles or or what have you depending on the situation. Yeah and this is really common where you'll see if you look 355 days out let's say for maybe you're looking for, for example, Japan Airlines business or first class, you might find a couple seats that far out, but if you look 330 days out, when you could use your American Airlines miles or Alaska miles to book it, then those seats aren't available anymore because people have probably snag them with other types of miles that can book them, book those flights further out. Yeah, so you'll want to check out.

out the booking calendars. Positioning flights, you may need to position to another airport. Yeah. So that's probably the number one thing that if your heart set on a big international trip, and especially if you want business or first class, the chances of finding, you know, a single booking that gives you the type of flight you want right from your home airport to your desired destination, that's a tough. one. I mean, it's not that it doesn't happen, but it can be really tough. So ideally, you're

open to, for example, departing from a different airport that you could get to easily than your home airport, or arriving at a different airport than your ultimate final destination and then booking a separate positioning flight to get to your ultimate destination. Yeah, and sometimes you've got to do a little bit of both, depending on your situation. But when it comes to positioning flights, we've got a few tips to keep in mind. And the first one up is to leave some room for error, leave some room for a flight delay or cancellation. I hate to book like the last possible flight as my positioning flight because then if something goes wrong with that flight, I might lose the really valuable big international award that I have. So I tend to prefer to position the night before when I can.

This, to me, is the perfect time to use a hotel free night certificate for a relatively affordable price. I pay the annual fee on some credit card that comes with a free night certificate, and I'll use that for an airport hotel near the airport where I plan to depart. So I prefer to do that, but that's not the only way to do it. There are other things to consider with this, like airport connection times. Do you have some experience with those? Yeah, I mean, so, you know, if you're trying to book a connecting flight, same day, then, you know, you've really got to take into account how much time will you likely have at the airport where you're going to be switching from your positioning flight.

Let's say you want to fly out of JFK, for example, and then that's not your home airport. So you position to JFK, and then you're flying out from JFK. JFK on your big international trip, you need to find out, you know, which terminal are you going to be arriving at at JFK, for example, because if you have to change terminals, you've got to factor in that additional time to get to your ultimate gate so you can check in on time. The timing difference varies so much by airport and situation. So to give you an example, if you're positioning on your way home, like I did once flying back from, I don't know, somewhere international to Atlanta. And then I had a separate positioning flight booked on Delta to Detroit. And I noticed that we would be landing in Atlanta a little bit earlier than I expected. So I wanted to change my Delta flight to an earlier Delta flight.

And I did that or I tried to do it right before getting off the plane in Atlanta. But it turns out like Atlanta's international terminal, at least at the time that this happened to me. Maybe they've fixed it by the time you listen to this. But is like a madhouse for clearing immigration customs and all that. it just takes forever. So as it happened, I was still able to make that flight, but that involved a lot of running. And literally, I think I only made it because someone else was late. And so they're holding the door open for that other person, and I managed to get on because they kept it open for them.

But you don't want to be in that situation. So make sure you have plenty of extra time and do some research about the airport. where you're connecting if you have anything less than like four or five hours planned in. So if you're flying on a single booking and connecting somewhere and your first flight is late, so you miss your connection, because you booked it all on one ticket, you're protected. You'll get help in rebooking that next leg so that you'll eventually get to where you need to be. Now, of course, you might not get there on time for whatever you're trying to get there for, but you will eventually get there.

When you're booking separately like this, you're not protected in that way. So you really do have to, you know, make double sure that if things go wrong, you know, with your positioning flight, for example, that you have some backup plan to handle that. Yeah, so let's talk about backup flights. Before we do real quick,

this is kind of included with what Greg was just saying, but when you're doing your research, check and see if the terminal that you're going to arrive at and the terminal you're going to depart from are connected airside or not. I think Greg kind of insinuated that with going through immigration. But even if it's all domestic, if they're different like JFK is a great example, you're often going to have to go through security again at the new terminal, whereas some other airports, most of the terminals are connected airside. And so that can make a huge difference in terms of how much time you need to have there. And I know you made that point, but I think. it's probably worth repeating for anybody who's not familiar with different airports and how those connections work. Totally. But back to the backup flight. Yeah. So I will, if I'm positioning, I will usually book a backup plan, a backup flight that can easily be canceled. A lot of the U.S. base carriers allow free cancellations on flights booked with miles. And so I'll take advantage of that to book a backup flight that can easily be canceled. So for instance, this summer I have one of these

situations where we are actually going to be flying to New York City from somewhere else the same day that we're departing for Europe from New York. And so I have two flights booked and we'll hope to get on that first flight. I mean, we'll definitely be at the airport in time for it. But if that first flight were to get canceled or have a mechanical problem or get severely delayed, I've got another flight booked that departs a little bit later, but would still get me to New York in time for my big international award. Now, when you do something like this, if you're going to book backup flights, things to be aware of are that you want to use a different airline and a different program, or you might risk one or both of your positioning flights being canceled, and it's not always

intuitive as to which one. So for instance, if you were booking a flight on United with your United Miles, you don't want to book another United flight probably, certainly not another United flight with your United Miles, but I would probably not even advise. doing it with partner miles just because if they notice it's the same person booked on two different flights united is likely to cancel at least one of those and you don't know if it's going to be the one you ultimately want or that last minute backup that you'll take only if you have to so use different airlines book a flight with united and a flight with southwest or a flight with american and a flight with delta etc yeah and and this thing about not booking the same airline that's not

hypothetical i had that happen to me where i booked a flight with united miles on United, and I also booked a United flight with A&A, United noticed that I was going to be on two flights at, you know, same day that couldn't possibly like work together, and they canceled the one book through A&A. Yeah, yeah. So you see, and that could cause you an issue, particularly if that is tied in any way to a bigger reward. So you want to avoid that. Also, if you've never done this before, or maybe it's worth mentioning not being thrown for a loop when you get to the TSA checkpoint and they ask which flight you're on. I've had this happen to me several times lately, actually, because I was booked on a backup

flight and the TSA agent will see that I'm booked on more than one flight and ask me what flight I'm taking. And so I'll just explain that I have a backup flight booked just in case the first one gets canceled. But the first time that happened, I was surprised that the TSA agent knew that. But it makes sense that they have all of those types of records. And again, it wasn't a problem. Just honest about what I was doing and no issue there.

But it's worth at least knowing that you may get asked a question about that. So, you know, no, that could happen. But no problem there. So I book backup flights often when it's important. If I really need to get somewhere, then I will book a backup with miles. It's freely cancelable. I just feel like it's worth doing if you're positioning for an award that you're going to have a hard time replacing. Yeah.

And the biggest tip I have for dealing with positioning flights and the risks involved in it is avoid checking bags if you can. When you check bags, even if you're flying through an airport where you could connect to the other airline airside, you might have to exit security. to go get your checked bags from the first airline and then go through security again with the second one. So that's a big deal. Of course, you know, check bags can delay things, can, and they could get lost and all kinds of things can happen. Now, I know for some travelers who travel with lots of stuff, that could be really hard to deal with. So, you know, if that's you, I would look very seriously at making sure that you do your positioning day before so that you have like overnight to deal with any problems that occur. Don't jinx me like that, Craig. I've got that

same day backup flight book this summer. And of course, we're checking bags. We'll see. Hopefully I got enough time in between. But yeah, I mean, that is a good tip that you want to avoid that if you possibly can. So what about if you can't find a positioning flight, don't have a positioning flight. You know, for instance, my local home airport is Albany, New York, and Boston is an airport that I often consider booking international flights out of, but there's no flight from Albany to Boston. So positioning isn't really an option via airplane. What else could I do? Yeah. I mean, you know, don't forget that driving is an option. Now, the problem with that is then you're probably, if you're driving your own car, you're probably leaving at an airport that you didn't really intend to go back to at the end of the

trip. So in that case, consider a one-way car rental. Those can be extremely expensive, but there are tricks to avoiding that. For example, if you get Nationals free day from their rewards program, then you can book a one-way just for the one day. So you get that free other than some taxes you have to pay. So that's a good way to do that. Of course, if you have train available to you, you know, I think that's especially a good trick when positioning in Europe because there's trains all throughout Europe. You can often get from one city to another that way. And, you know, and buses, of course, are an option as well. Yeah. And with that one way rental, another thing I'll mention is that check if your employer has any sort of rental car benefits, rental car discount code.

because sometimes those discount codes can be used on leisure travel also, and they may have some benefits like it's not uncommon for some corporate programs or institutions to offer rentals without any one-way fees. So depending on who you work for, you might find that it's significantly cheaper for a one-way rental with your corporate code or institutional code, whatever that might be. So it's worth checking that if you have access to something like that. All right. We'll be right back after this with more of our main event. 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 beginners guide. And we're back with even more tips on how to book. possible flight awards. Our next tip is that some loyalty rewards programs reserve more space for their own members on flights than they do for partner awards. So this is becoming increasingly common.

EVA is a really good example where flights to Asia can be really hard to find awards, especially in business class. But if you have EVA's own miles, which you could get from a few transatlantic. transfer transferable points programs, you will have much better award availability for that. Cathay Pacific is similar. Edihad does the same thing. So we see this a lot with Asian carriers where, you know, like I said, they just reserve a lot more space for their own members. But it's often true for just about any carrier. Yeah.

And, you know, the thing with some of those programs is that the award pricing might be a little higher than what you could get through other partners. So, for instance, Cathay Pacific, you're going to pay more Cathay miles for a Cathay Pacific flight than you might, if you booked that via, let's say, American Airlines or Alaska. But the problem is you probably won't find that flight available via American or Alaska, and you may well find it available via Cathay Pacific. So it might cost you a little bit more, but you might actually be able to find

availability so it can be worth a few more miles. Yeah, yeah. Another thing that we're increasingly seeing is programs, that reserve the cheapest award space for their own elite members and or cardholders. We see that with Air Canada Aeroplane, where they do both. Their cardholders and elite members can get better access to cheaper awards. United, cardholders get better Polaris business class, saver award availability. And another example is Air France KLM, where they reserve for their platinum members better award space and also things like the ability to use points to book their first class, international first class awards.

So, you know, that's just something to be aware of. I guess, you know, I'm not necessarily recommending you go out and try to become elite with one of these programs, just in the hope that you'll have. better award space, but, you know, maybe you already have a credit card with one of these or you already have elite status with one of these and maybe you wouldn't have thought to look for better award availability by logging in and checking there. Yeah, that last piece is really the thing, right? Because even years ago, I don't have a United card anymore, but when I did have a United card, there were times when I just didn't even think to log in and do the search. That just wasn't my habit. And I realized that I probably

missed out on some award availability that I would have seen. I remember that one day in particular when I logged in without even thinking about it and I was like, oh, right, right. I have access to more awards. I should be logging in all the time when I search. So it might not be top of mind for you, particularly if you're newly, you know, a card holder with United or newly elite with Air France or whatever program it may be. So I think that's a really key tip. Some programs also offer the ability to book more awards for more points. So, you know, obviously we all hope to find saver award availability and pay as few points as possible. But sometimes the schedule or the destination or some other piece is more important to you. And you might be willing to pay more

points in order to get the particular award flight that you want. And so there are programs like Qatar Airways Privilege Club that offers more space for more points. So they'll have different awards that are available and you just pay more for the particular award you want. Or Alaska does this with awards on Qatar, where they have some access to sort of savor level pricing, but then they have more access to flights that cost more miles. And these are, again, just examples that could change over time. But they're good examples of the situation as it stands at the time we record this anyway, where you do have access to more award availability when you use more miles with some programs. And that's not true in all programs. Well, while it's increasingly true on U.S.-based carriers for

their own flights, it's not true for all of them that they get expanded award space on their partners for more miles. So it's worth doing a little research to figure out which programs might offer you the chance to book the award you want for some additional miles. Yeah. Yeah. I think the Qatar one is especially relevant, assuming it stays true by the time people listen to this. because, you know, Qatar Miles Avios you can get by either transferring directly to that program or transferring to another Avios program like British Airways and then moving those points over to Qatar. And I'm pointing that out because transfer bonuses to various AVIos programs are really common. And sometimes we've even seen like from Built, for example, as much as 100% transfer bonus.

And so if you're looking for that, you know, to fly, guitar cue suites in just the right time, and you see, oh, you know, yeah, sometimes it's available from the U.S. for 70,000 points. But at the time I want to go, it's 140,000 points. That seems like a lot. Well, maybe it doesn't seem like so much if you could get a big transfer bonus and make it, you know, it could bring it into. you know, the realm of what you can afford with your points. Yeah, that's a great point. All right. Another thing, another tip, another piece of information to keep in mind is Married Segment Logic. Now, this one's one that, I don't know, it's, it's unintuitive. I think if you're not familiar with it, I think that you, well, first of all, you hear the term Mary Segment

logic and maybe not know what it means, but I think you'd be even more surprised when you dig into this and find what might be available. Yeah. So what it means is is flights are priced not based on the exact routing, but, but the, like, beginning and endpoint often. And weirdly, that's sometimes true with award availability. And to understand why that's weird, I'll give you a specific example that I saw once, I found when booking with, I think it was Alaska Miles, going from San Diego to Tokyo, was available to fly.

I think it was Japan Airlines business class at the safer level using Alaska Miles. But that was flying through L.A. So it was San Diego to L.A. to Tokyo. And but I really just wanted to fly L.A. to Tokyo and that was not available. And so that's an example, Married Segment Logic. They're trying to get people, you know, they're encouraging bookings from San Diego or actually San Diego is an example. I don't even know if that was the actual airport. It was some other airport besides L.A., but we'll say San Diego. They're trying to, they're encouraging people to book from San Diego to Tokyo. And, and,

So therefore, the LA to Tokyo leg becomes available at that saver level award, even though you can't book it as a nonstop. Now, these are, these situations are not uncommon, believe it or not, but they're really hard to find. Because, like, how would you know to look for flights from San Diego if that's not where you want to start? Or how would you know, maybe you would find the other. way. Maybe you'd find L.A. to, you know, Osaka, but not to Tokyo, for example. How would you know to look for that? And it's not easy. One way that I've found helpful is to use, there are various award search tools that use pre-cashed results, where they've searched lots of, lots of different routes and they store the results and then they allow you to do very broad searches.

Like, for example, say, I want to fly from the United States to Japan as an example. And those tools have the ability to find some things like what I described when a tool doing live searches, which you would just think to put in L.A. to Tokyo, right? you wouldn't find it when you're doing that with a live search, but you might find it with one of these pre-cash tools. In my experience to date, as we're recording this, in May of 2026, the points you had Daydream Explorer has been my go-to for that type of search. It seems to do the best at coming up with valid results. The free version of the tool gives you the full power of that Daydream Explorer capability. So that's really good.

And I should also mention they don't, none of these tools store every possible search that can be done. They're storing, you know, I think some of them automate some searches, but a lot of them just store the searches that their members are actually doing live searches of and then making those results available to you to query. So by the time you see it, it might no longer be true. But conversely, you might see a pattern. Like, let's say you're looking over several months and you see, oh, there's some flights from San Diego to Tokyo via L.A. that are available, but not during the dates I want. At least now you know that pattern. And then you can look at the dates you want. Search from San Diego to Tokyo using any of the word tools. And maybe you'll find that it is actually available on the date

you want. It's just that the tool you're looking at didn't happen to pre-store those results. Yeah, and along the same lines, this is where kind of being a hobbyist can work out to your advantage. If you're somebody who just enjoys looking at this stuff, then you can pick up pieces of knowledge that you can apply in other situations. Another similar example to this is that a lot of the U.S.-based carriers have kind of variable pricing these days. And so, for instance, Los Angeles to New York and business class on American Airlines might be available to book with your American Airlines miles, but it might cost a bajillion miles. However, at some point, someone gave me a tip, and I can't remember which airport it was anymore. And it doesn't matter because it doesn't work

anymore, this specific one. But let's say it was Los Angeles to JFK to Bradley, Hartford Airport. That wasn't it. But something like that. A route like that was pricing all the time at 19,000 points in business class. Yeah. And so, you know, knowing that, there were lots of times I looked at that different times of the year where I was like, wow, you can get that just for 19,000 miles in business class and get that lie flat seat to New York. So knowing, recognizing, if I had been looking at one of those daydream explorer type things

and seeing, oh, wow, interesting. Flights to Hartford are often way cheaper than just the flight from Los Angeles to New York. And again, that's not a true statement. Hartford is not some secret sauce. sorry, but using those Daydream Explorer tools, you can find those types of things where you may see, oh, well, this consistently prices better with this particular connection, or at least it is right now, and knowing that can help you. Because even if I saw that on the Daydream Explorer for days when I didn't want to travel,

that piece of knowledge might come in handy one day when I do want to travel from Los Angeles to New York. So I think playing with that stuff can really be useful for just finding all of those sorts of things, not only availability, but also pricing oddities like that that just work out really well. Now, one big downside of this whole thing is usually if you book something like that, you're going to have to actually fly it, you know, especially if the part you didn't want is at the beginning, like that San Diego to L.A. to Tokyo part. Although I will say it's worth calling the airline you booked with, not the airline you're flying, but the airline you booked with to see whether you can drop the leg that you don't want without repricing the award. I was actually able to do that

not that long ago with an American Airlines Award, but that award was entirely on partners. I don't think it would work with, like the example Nick was giving, where you're actually flying American Airlines itself. I 99% sure they would reprice that entirely if you're, you're going to. try to drop that last piece. Right. But if you travel carry on only and you miss that flight, then they won't probably retroactively reprise it if you do it one time. So if the segment you don't want is at the end of your, the part you do want, you can potentially,

you know, just forget about that leg. There are risks to that. We've talked about that in previous shows around when we talk about skip. lagging, where you purposely book extra legs, basically to make flights cheaper and don't intend to fly that last leg. There are risks to it. So make sure you do your research about that if you're thinking of doing it, because we're not going to get into full details.

Right. And that's something you want to repeat over and over again. But you can listen to other shows about that. All right. So let's see. Next up, consider programs that allow a stopover. And this is a technique that's come in handy for me a number of times because maybe, for example, let's say I'm in New York and I want to fly to Johannesburg. I want to go to South Africa. But I can't find anything that's available altogether, like an itiner, one single itinerary from New York to Johannesburg on the days when I want to travel. I might consider something like looking for just JFK to Frankfurt and separately, looking for Frankfurt to Johannesburg sometime within the next few days thereafter. Because maybe the day I can land in Frankfurt, there isn't availability to continue on to Johannesburg,

but maybe two or three days later, maybe there is a flight available. And then you can consider using a program that allows stopovers, like as we record this, Alaska Airlines mileage plan, or I'm sorry, Alaska Atmos rewards, excuse me. And Air Canada, Aeroplane and Air France, KLM are all programs that offer stopover benefits. And so it varies as to how that works with each program and how you'll book it. But sometimes that makes it possible, particularly for me as a family traveler, I need four seats usually when I'm looking. And so I might need to kind of expand my search a little bit and look at separating those

legs and finding four seats on two different days that don't necessarily line up. But if I can use a program that allows a stopover, I can increase my odds of finding an award that works. Now, obviously, it depends on how much time you have to do that kind of thing. a number of days you can afford to put in between. There's a lot of variables there, but this is a technique that, again, particularly as a family traveler,

I found to be handy. Yeah, and, you know, this isn't really about finding impossible awards, but another advantage there is when you, I'll just give a really specific example because Nick mentioned JFK. Often when I look for international flights from Detroit,

I find awards that take me, first segment goes to LaGuardia Airport, and then the next segment is flying from JFK or Newark to an international destination. And, you know, I don't like to do that, especially if the layover is only a couple hours trying to get from one of those airports to the other can be, forget about it. However, if you can bake in a layover and, you know, stay overnight, in the New York area, then you can book it all on one award and not have to worry about that short connection. So that would be nice. Yeah, definitely. Definitely something to look for it. And by the way, on that note, now that you mentioned that, be aware that the maximum connection time, the

maximum layover time can vary depending on the program you're booking in the type of award. as a, for instance, a domestic award on United, most programs will allow up to a maximum of a four-hour connection, and then they might price it separately or charge you something additional. If it's more than that, again, that varies from program to program. But if you're on an international award, usually you can have up to 24 hours between flights without that being a stopover. That's just a layover if it's less than 24 hours. And I've had good success with Air Canada Aeroplane in particular in finding maybe I found an award that gets to Europe. up and then I've got a 23 hours to find another award that connects on from there and and book something else that way. So definitely that's that's a great point. Your example of New York,

it certainly is applicable for those New York changing airport situations, but it could be just as applicable in other cities as well. Yeah. Yeah. And really good point that it doesn't have to be a stopover award in order to do what I'm saying to get an overnight. You just have to make sure you pick pick the right flights so that you have a lot of time in between and potentially overnight. The next tip is about using alerts. So a lot of award tools allow you to set flight alerts to let you know when award seats open up on the route you're interested in. And this is so key because not everybody gets this when they're starting out that award space isn't a permanent on-off thing on flights.

Like whether there are award seats available on any given flight, you know, yes, they tend to open up at the beginning of the schedule. So like when a flight is first available to be booked with cash, often there are a few seats available also for awards. But also all throughout the years, you lead up right, right until the flight flies, the availability of seats changes. Now that changes for a number of reasons.

One is some people who had booked awards might cancel them. Also, the airline might realize there's less demand for that route and that time than they were expecting. So they open up more seats for awards, especially as it gets closer in to departure. Often airlines will say, oh, this isn't anywhere near full. Let's open up more seats for awards. that kind of thing happens all the time. And yes, you could search over and over again every day, or you could use an award tool to set an alert, set and forget,

and let it alert you when your seats become available. Absolutely. Yeah. And I think it's worth mentioning there that even the free version of some popular award search tools allow the ability to set alerts in some cases. It's worth doing some research into that. may not even need to be paying for an award search tool in order to set an alert or two or three. It's going to vary from one tool to the next. But I find these so useful. I used to be an obsessive award searcher where I would just constantly be searching for awards on both trips that

I haven't booked but want to and trips that I have booked, but I'm just curious did something better become available. And I love being able to set an award alert and just have something come to my phone when availability opens up. Because a lot of of times it will if you use these award alert tools. And now I say a lot of times it's obviously going to vary because maybe demand is just going to be really high on the dates when you want to travel. But this is really a tool that I'm glad to have and keep and hold on to. Yeah. Yeah. All right. Lastly, don't forget that you can pay cash for flights as well. Sometimes it's easier to find good cash prices for desirable flights than mileage prices for those same flights.

And when that's the case, even if you want to pay with points, you might have opportunities to do so at slightly elevated value. There are, you know, not as many as we record this today, not as many opportunities to get outsized value with your points when booking flights as there used to be. But there are still some that exist at the time we're recording this. If you're booking a U.S. carrier, you might be able to get a really. good rate using your business platinum card because of its sort of rebate on points bookings with your preferred airline. Another example, Chase Sapphire Reserve card has this points boost feature, which at the time of the recording, for business class international flights, you might be able to find a boost of a 2x boost, which means you have to pay half as many points as you

would if they were giving you one cent per point value. And, you know, and then there's other, you know, less popular programs that sometimes offer like 1.25 or might offer a fixed point redemption rate for flights of up to a certain price, you know, that kind of thing. So if you have any of those options, it's probably worth looking at. But also, you know, if things get really bad, if you could find a flight that's not that expensive. Maybe you look at this as an opportunity to earn points in miles rather than spend them if you really have to. Yeah, and to kind of just add one more tiny piece on this that, you know, if it's maybe a backup to a backup kind of a situation, take a look at what the difference in price is to book a refundable, a paid ticket. You know, sometimes maybe in a situation

where the refundable fare isn't all that much more and might be worth booking if this is kind of a backup plan because you need to have some other way to definitely get there on time. So, you know, similar to booking with points, believe it or not, there are refundable fares you can book with cash too. So I know that doesn't feel as common in a lot of cases, but they exist. You know, you know, that's, that's an important topic overall. We mentioned booking backup flights in the context of positioning flights, but what, what I do regularly is, you know, if I'm looking a big international trip where I know I have to be there by a certain date, for example, I'll often book an award or a refundable cash rate that will get me there,

even if it's not ideal for what I want. It's one of those sort of like, good enough if I have to bookings. That way I feel more comfortable, you know, setting alerts and just waiting until the ideal thing opens up. Yeah, well, and that probably adds one more thing that we didn't have. in our outline either. And that is, strike while the iron is hot. Don't necessarily, I always tell people, I don't plan my trips based on finding round trip availability, particularly for these impossible to find awards. So if you're looking to go somewhere like Australia or Asia these days,

or you want to go during a school break or whatever, if you find availability for one direction, then at least very seriously consider just booking that, particularly with Miles where you know you'll be able to cancel if you just can't possibly find the other direction. But I don't wait for the stars to align and get both directions at the same time. That's sometimes really difficult to do. So I'll just hop on the one direction and set an award alert for the other direction and hope to find that later on. Yeah, yeah. And, you know, especially you can combine these two things that we're just talking about. So let's say you find the, um, a great award flight return from your spring break time period, which is always a tough to get time to book awards, even if it's not easily canceable

or has an expensive cancellation rate, you know, book it if that works really well for you and book a good enough outbound flight as a placeholder so that you know you'll get there and you'll know you'll be able to take that return, but do all these other things, set up alerts, you know, try to find a better outbound flight before you take. take off. And it's not unusual for me to change my plans a couple days before the actual departure flight because something great has finally opened up. That's always a hard piece of this hobby to kind of communicate to somebody who's new to the hobby and or explain or get somebody used to, somebody that's maybe traveling with us and say, well, this is the plan right now.

But it could change as we get closer to departure. But I mean, it's true. If you can, if you can build that kind of flexibility or get used to, get accustomed to that kind of flexibility, then it opens up so many more possibilities because you can take advantage of those great opportunities when you see them and, again, be okay with the good enough for now and changing later on. I think that's a terrific point that is probably maybe even the biggest key to booking the truly impossible awards is being able to do that and flexible about changing plans once something better comes along. 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 us. Send that to? Send it to mailbag at Frequentmiler.com. Hey guys, Aaron Miller here from Armchair Explorer, and I just wanted to let you know that our new series is out now.

We've got kiteski across Antarctica, Aboriginal storytellers, and the craziest whitewater race in the world. We're going on a bucketless hike across Italy. We're going to the Fjords of Norway in search of the Northern Lights and lots, lots more. Our goal is to take you on the trip of a lifetime every single week. You can find Armchair Explorer on Apple Podcasts, Spotify, wherever you're listening right now and at voyescape.com. The New York Times named the Fromer's Travel Podcast one of the 13 best for travel. Why did they like it?

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