November 28, 2022

Bali Trip Villas

The Devoted Travel Specialists

Podcast #811: The Secrets to Booking Cheap Flights

Travel can offer a lot of good: memory-making adventure, mind-expanding experiences, and plenty of fun and relaxation. It’s not surprising then that most people say they’d like to travel more than they do. What’s keeping them from fulfilling that desire? Well, one obstacle, especially these days, is that the high price of plane tickets puts flying out of reach.

My guest today can help you surmount this obstacle so you can get away more often. His name is Scott Keyes, and he’s the founder of Scott’s Cheap Flights and the author of Take More Vacations: How to Search Better, Book Cheaper, and Travel the World. Today on the show, Scott shares how scoring cheap flights can help you travel more often, the advantages of taking more frequent vacations, and the psychological benefit of planning your trips well in advance. We then get into the misconceptions people have about ticket pricing. From there we turn to Scott’s strategies for booking cheap flights, beginning with why he recommends adopting a “Flight First” rather than “Destination First” approach. Scott shares the “Goldilocks” time window when cheap flights are most likely to pop up, the benefits of building flexibility into your itinerary, the days that are typically cheapest to fly, and his favorite search site to look for flights. He also explains how to use the 24-hour rule and Southwest Airlines as arbitrage in getting better prices on your tickets, and how to employ what he calls the “Greek Islands Strategy” to save money when flying internationally. We end our conversation with how to take advantage of “mistake fares,” and whether the high prices you’re seeing this summer are here to stay.

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Read the Transcript

Brett McKay: Brett McKay here and welcome to another edition of The Art Manliness Podcast. Travel can offer a lot of good, memory making adventure, mind-expanding experiences and plenty of fun and relaxation. It’s not surprising then that most people say they’d like to travel more than they do. What’s keeping them from fulfilling that desire? Well, one obstacle, especially these days, is that the high price of plane tickets puts flying out of reach. My guest today can help you surmount this obstacle so you can get away more often. His name is, and he’s the founder of Scott’s Cheap Flights, and the author of Take More Vacations, how to search better, book cheaper and travel the world. Taking the show, Scott shares how scoring cheap flights help you travel more often, the advantages of taking more frequent vacations, and the psychological benefit of planning your trips well in advance. We then get into the misconceptions people have about ticket pricing. From there, we turn to Scott’s strategies for booking cheap flights, beginning with why he recommends adopting flight first rather than destination first Approach. Scott shares the Goldilocks time window when cheap flights are most likely to pop up, the benefits of building flexibility into your itinerary, the days that are typically cheapest to fly and in his favorite search site to look for flights.

He also explains how to use the 24-hour rule in Southwest Airlines is arbitrage and getting better prices on your tickets, and how to employ what he calls the Greek island strategy to save more money when flying internationally. We end our conversation with how to take advantage of mistake fares and whether the high prices you’re seeing this summer are here to stay. After the show is over, check at our show notes at airwave.is/cheapflights.

Alright, Scott Keyes welcome to the show.

Scott Keyes: Thank you so much for having me. I’m excited to be here.

Brett McKay: So you are the founder of Scotts Cheap Flights, where you highlight cheap flights that are out there, you’ve become the guru at finding really cheap flights, and you got a new book out where you highlight all the tips you’ve learned over the years of finding cheap flights. How did this happen? How did you end up becoming the cheap flights guru?

Scott Keyes: Well, it started off when I went to school and studied cheap flights, I got my degree in cheap flightology and… No, no, no, I actually, this was all a very serendipitous occurrence for me. I never in my life would have been imagined that I would become an entrepreneur, much less a cheap flight entrepreneur. I studied writing in political science in college, I was a journalist for a while in a previous life, and I really kind of but it happened backwards into this life where they say that necessity is the mother of invention. While I was somebody who out of college, had huge dreams of wanting to travel to Europe and Asia and elsewhere, but basically no money to do it. And so I knew somehow people are out there getting cheap flights, but at the time, I had no idea how they were doing it, and every time I was searching for flights, it was like, they all were expensive, unaffordable, how were people doing this? And so what I ended up doing was really kind of putting on that journalist hat and scratching that itch of why is it that airfare is so volatile, how do you put yourself in a position to get those cheap flights when they pop up?

And this all then culminated a year or two later when I got what is still to this day, probably the single best deal that I’ve ever personally gotten, and that was non-stop from New York City to Milan for $130 round trip. This was a steal. There’s probably a flight that they meant to sell for $1300 and forgot a zero at the end, but when I booked it, it was $130, and it was probably the best deal I’ve ever gotten. And so, by taking this wonderful trip to Northern Italy and going skiing in the Alps and hiking in Cinque Terre, not only did I end up having this wonderful, incredible trip, but when I got back, oh my… I guess word had spread to all my friends and co-workers and they kept coming up to me, “Hey Scott, I heard about that great deal you got. Listen, next time you find a deal like that, can you let me know so I can get in on it too?” And so rather than trying to remember every single person I needed to let know next time I found a deal, I decided, well, why don’t I just make a simple little email list and this way I can let everybody know at the same time. In that moment, Scott’s Cheap Flights was born, but I had no idea ’cause I wasn’t an aspiring entrepreneur at the time. I was just somebody who wanted to solve this problem of letting everybody know when I found cheap flights, but then over the next year or two, it grew and grew until it was finally time to think about turning it into an actual business.

Brett McKay: And here we are today talking to you about cheap flights.

Scott Keyes: Exactly. Look, everybody else says they have the coolest job in the world, but I get to find cheap flights every single day and help people make their vacation dreams come true. So I would at least like to put my hat in the ring for that one.

Brett McKay: So you’re helping people find cheap flights, not for the sake of finding cheap flights, you’re really passionate about this ’cause you want people to take more vacations, in fact, that’s what the title of your latest book is called, Take More Vacations. Let’s talk about that. Why do you think people, particularly Americans, need to take more vacation? What is the state of vacationing for Americans?

Scott Keyes: So there are a few reasons why. First reason why is because everybody says they want to. Everybody says traveling and taking more vacation, it’s one of the top New Year’s resolutions every year, it’s one of the top. And when you look at survey data of what people wanna do when they retire, it’s always up there number one, number two, everybody desires to take more vacations than they actually do. When you look at the data on how many vacation days people have actually been taking, it’s basically been on a downward slide for the past 25 years. In the late 90s, people were taking on average 21 days of vacation a year, and the most recent data was more like 17 days, 16 days. And for millennials, it was under 15 days per year of vacation. And so everybody wants to take more, and yet we’re taking less and less, and so part of it was to figure out, “Well, why is that the case? Why isn’t our actions lining up with our desires?”

And one of the things that I really was struck by is how much the stress and complexity of trying to book flights is weighing on people’s ability to take vacations. That because airfare is the single most volatile thing that most people purchase, that ends up leading to a ton of stress, it is… Planning is paradox, it’s probably both the most enjoyable part of a trip, but also the most stressful part for most people, and I think that’s actually causing people to take fewer vacations than they would otherwise because they seem to only see expensive flights because they don’t know if I don’t… If I see this fare today, should I book it? Will it go up tomorrow? Will it go down? How about a month from now? It ends up just leaving people much more anxious about inactivity that is theoretically supposed to be one that’s supposed to take their anxieties away. And so partially it’s just trying to do this thing in service of what people say they want, but really at the end of the day, the reason why I think people ought to take more vacations is because I think you end up enjoying those vacations a lot more as a result.

People, I think, make a mistake of thinking of travel and thinking of vacation as just something that you go do to relax, to sit on the beach and take your cares away, and that’s fine, there’s nothing wrong with sipping a cocktail on the a beach, but I would argue that traveling and vacations are actually more like a muscle where the more you do it, the better you get at matching the types of destinations, the types of trips and the types of activities to your individual personality. And so what I mean by that is when you look at people’s satisfaction with their vacations over time, it actually goes up as they take more vacations because they get better at figuring out, will I enjoy a trip to the center of Paris, all the hustle and bustle, or would I prefer something more in the country side?

What I would I like to travel to somewhere where there’s maybe a ton of pedestrian infrastructure where I can walk around, or would I rather be somewhere where it’s very nature-focus? There are tons of different types of trips out there that folks can take, but it’s difficult to figure out which one is right for you until you start to just take more of them and test it out and see what you… What vibes most with you rather than what vibes most with the average traveler.

Brett McKay: And finding cheap flights allows you to take more vacations. I think most people… Because flights, they think, “Oh man, they’re so expensive. I can only take one big vacation a year.” And because you only do it one time a year, you’re not able to find out what do I really like? And it also, I think taking that one big vacation a year, it puts a lot of pressure on that vacation, it has to… If it’s not out of the park, you’re gonna be disappointed, like, “Man, I just wasted a lot of money and time.” But if you take smaller, cheaper vacations, you increase the chances of you having a better time.

Scott Keyes: Yeah, that was one of the biggest revelations for me on this $130 trip to Milan was that because I got such a deal on the flight over, the entire experience of the trip was so much different, it was like this weight had been lifted off my shoulders. Where everything felt like it just had a halo to it, it I had some salt added, I didn’t have that pressure to enjoy myself, and every single minute I could relax and kind of take things a bit slower. I could frankly spend a little bit more. I could get that truffle linguine, I could buy that first class train ticket rather than sitting in coach, I could splurge on the better seats for the AC Milan soccer match, I could do these things because I had saved so much on the flight over there. And so the cheaper the flight, I think the better you time you end up having on the vacation itself, because you can take that money you saved and devote it towards having a better trip, but also because you don’t have the same sort of pressure. So I think it works both on a financial standpoint, and as you mentioned on the sort of quantity of vacation standpoint. If you take one big trip a year, that’s putting a lot of pressure on that trip to enjoy it, making sure that this is…

All the sort of anticipation and pressure on this one trip, and then maybe you get there and things don’t go as planned, maybe there’s thunderstorms, maybe you miss the boat or the flight or something. I don’t know, you get… You lose your wallet. Like things happen on travel where all of a sudden if it happens during this one trip, that’s your entire vacation budget, time budget for the year, whereas if you break that time up into two, three, four trips on the year, not only is it much more spread out, but then the hangover of coming back home from your vacation, it is just a much different experience when you come back from that one big trip and it’s 49 weeks until your next vacation, buddy, that is a tough, tough outlook. But if you come back and it’s just three months until your next trip, well, that’s totally doable. You can already get busy planning, planning out what you’re gonna do at three months from now on your next trip, and so that’s why I’m such an advocate of taking more vacations using cheap flights as a way to get them, and then being able to not only enjoy yourself more on the trip, but also being able to test out the places that you go further down the list. If you have one trip a year, you probably have to go to the big hits, you go to Paris and London and Tokyo.

But if you have three or four trips a year, you can take a chance, you can take a flyer on going to Albania, to Trinidad and Tobago trend, to Taiwan, places that are kind of further down the traditional list, but might actually speak a lot to you personally. And some of the best trips I’ve had have been those sort of be-less see-less places that are not at the top of the traditional tourist circuit, but I have been some of my favorite trips to Trinidad and Tobago, to Taiwan, to Lithuania, and that I’m so glad I was able to see those places, which I might not have if I only traveled once a year.

Brett McKay: Yeah, so I think feel like too, when you go to the big hits, you go there and you’re like, “Oh, this looks like the pictures I’ve seen on the internet,” and it’s kind of a let down.

Scott Keyes: Yeah, yeah, especially something like the Eiffel Tower, The Mona Lisa…

Brett McKay: The Tower of Peace.

Scott Keyes: It looks exactly like I expected it to.

Brett McKay: Yeah, The Tower of Peace, it’s leaning, alright. So I also like to… So there’s all these… You should highlight this research about when you take vacations, it’s great for your psychological health, it’s great for your physical health, but you devoted this chapter about the anticipation factor of vacation. So how thinking about going on a vacation, actually, that’s probably one of the most enjoyable parts, but talk about what happens when you have something to look forward to, like a vacation to look forward to, to your mental health?

Scott Keyes: That’s right. Look, I think a mistake that folks make when thinking about travel is we only think about travel as what happens on the trip itself. You’ve got a seven-day trip to Costa Rica, and you just think about it during those seven days, but if you actually look at the research of how people tend to enjoy their travels, it turns out we actually get more happiness and more joy in the weeks and months leading up to a trip than we do on the trip itself, and we actually get more joy in the weeks and months after a trip, looking back on it, than we did on the trip itself. And that’s not to say we don’t enjoy the actual trip itself, we do, but we get even more happiness before and after a trip, and I think a lot of folks maybe do themselves a disservice by buying into this idea of like, “Oh, a romantic, last minute get away. Oh, I’m just gonna book something for this weekend and go.” And that’s fine, there’s nothing wrong with it. I like being able to be spontaneous sometimes, but I think that undercuts some of the ways that you can really enjoy your vacation by planning it further out and giving your today self the joy of that anticipation of looking forward to it.

The great thing about daydreams is nothing goes wrong in them. When you’re actually on that trip to Costa Rica, I don’t know, maybe there’s a thunder storm, maybe, I don’t know, you get too close to some bad animal in the jungle, your taxi driver rips you off, something like that, but when you’re a month out from that trip, two months out and you’re day dreaming about hiking through the jungle, exploring the countryside, going to those coffee farms and those beaches, nothing is happening wrong in those day dreams. And so that’s why we tend to actually enjoy the anticipation of travel more than the trip itself, and why I think that folks should be taking more effort to booking their travels further in advance and booking more of them, so that way rather than just trying to book a trip a week before and then take it, and then there’s just this hang over, where you’ve got nothing to look forward to for months on end, instead book those trips three months out, six months out. I’ve basically always got a trip booked three or six months out, so I have something to look forward to today that I can be excited about in the future.

Brett McKay: Alright, so let’s talk about how we can take more trips, ’cause as we said, plane tickets are usually the most expensive costs in a vacation. Especially now, I’m sure people have tried to plan flights, they’re looking at it and they’re just like, “Oh my gosh,” like sticker shock. It’s like, “What’s going on?” So let’s… Before we dig into how to find cheap flights, I think it will help listeners to have a big picture overview of why plane ticket prices are so volatile, you check… You can check one day and it’s this price, and then a few hours later it’s like 10 times higher, you check and you can see an international flight is a cheaper flight than a domestic flight. What’s going on there? Why are prices so all over the place?

Scott Keyes: Yeah, airfare is the most volatile thing that most people purchase, and it’s something that’s really important to not fall prey to some of the classic mistakes that folks make of assuming that airfare is static. A lot of folks will think, “Well, a flight from, let’s say New York to LA is supposed to cost $300,” when in reality, it’s a wide range that it’s constantly swinging up and swinging down. The reason why airfare is so volatile is it has a few unique characteristics to it that’s unlike other things we purchase. It is what’s called a rival good, when I buy a seat on a flight, nobody else can buy that seat, or if I get it, nobody else gets it, there’s what’s called spoilage. So any unfilled seats when the door closes for that flight are spoiled, they get no money for those, so there’s an expiration date. And there’s unpredictability of if or when travelers are actually going to book those flights. And so airlines have to try to constantly be adjusting their price in anticipation that how many folks are gonna book that flight to LA if it’s at $300 or three months out? Not enough. Okay, we need to cut it to 250.

Oh, we’re selling plenty, we can jack up the price. It’s a very sort of volatile set of circumstances. And so the biggest thing that I think as consumers you can do is to stop thinking of airfare and flight tickets as something like a gallon of milk, where we think of air fare… When you think of a gallon of milk, you go to the grocery store, the price yesterday is gonna be about the price today, which is gonna be about the price tomorrow, and the price that you pay for a gallon of milk, or it’s basically gonna be contingent on how much milk you’re actually getting. A half gallon is gonna be a little bit more than half the price of a full gallon, etcetera, but airfare is nothing like either of those.

To give you one example, I remember looking once at a flight from Atlanta to Amsterdam, this is a flight over Memorial Day, I believe, and on Monday when we searched for it, it was $800 round trip. On Tuesday when we searched for the same flight, it was $300 round trip, and on Wednesday when we search for the same flight, it was $1300 round trip. And so it would have the… Airfare will have these wild swings where it’s not just slowly creeping up and down, it can change by and in an orders of magnitude day by day, and so the best thing you can do as a consumer in many cases, is to remember that today’s expensive flight can be tomorrow’s cheap flight and vice versa. And when fares are expensive, be patient, when they’re cheap pull the trigger quickly because that could change tomorrow.

And then the last thing I would say on this is, we talked about how the price of milk is largerly contingent with how much you’re buying. Airfare is not like that. I remember looking at a flight last year from… There were fares available from Pittsburgh to Tokyo for $202 round trip. This is an incredible fare obviously, but do you know where else was available to fly from Pittsburgh for $202 on the same dates? Philadelphia. And so it was the exact same price for the exact same wildly, wildly different amounts of flight distance. And so getting it out of your head that, oh, how far you fly has a direct relationship with how much you can expect to pay, that’s not the case with airfare. I think a lot of my job is really trying to get folks to unlearn those mistakes or unlearn their sort of assumptions about what airfare is supposed to be.

Brett McKay: Any other common misconceptions you see, either besides ticket price being correlated to trip distance, any other big ones you see that kind of mess people up?

Scott Keyes: Oh goodness. Clearing your cookies, incognito window. People swear by this, I cannot tell you how often I get yelled at to my face that I am absolutely wrong on this one, that it totally matters, you have to clear your cookies. I went ahead and tested this once to see, does it show a different fare? The thinking being, “Oh, if the airlines can see really… ” You’re searching for this flight, then maybe they’ll jack up the price to try to get as much money from you as possible so I went ahead and tested it once. I searched a flight from Denver to London, October 6th through 13th, and the fare came back as $442 round trip, I searched a second time, $442 round trip. I took hours of my data searches a hundred times in a row, and lo and behold, on the 100th time, just like the first time, it was still $442 round trip. I think the mistake people make is, they sort of Truman Show ask thing, where they see… Sometimes fares change when you are searching for them, and that’s because airfare, like we’d mentioned, is extremely volatile, but it’s not because the airlines are watching you… The individual breadth searching for these flights and deciding, oh, we’re gonna jack up the price on them, it’s because airfare is always changing, and in fact, I think the logic is backwards in some ways, because the way that most companies work is that if you engage in what’s called an abandoned cart.

Essentially, you’re looking at a pair of pants from Levi’s, you click on it, but then you don’t ultimately purchase it, they see that you clicked on it, they see that you didn’t buy it, their solution is not to jack up the price on those pants. Their solution, instead, is usually to hit you with a coupon code or some other way of discounting the price to try to get you to purchase in the first place. So the good news, it’s not gonna cause you to have more expensive flights to clear your cookies or to search in incognito, it’s just not necessary. It’s not gonna make any difference whatsoever.

Brett McKay: We’re gonna take a quick break for your words more sponsors. And now back to the show. Alright, let’s talk about some tactics to find cheap flights, and you say most people when they search for a flight, they use a destination-first approach when finding flights, but you are you that if you wanna find the cheap flights, you need to take a flight-first approach. So walk us through the difference between these two, and how does a flight-first approach help you find cheaper deals?

Scott Keyes: Sure, so let’s say you’re planning a typical vacation, Brett, and the way… If you plan your vacation like most people, you use what’s called a destination-first approach, and so it’d probably look something like this. Tell me if I’m off base here. You decide first, where do you wanna go? Oh, Paris, I’ve had it on my list for a while, it seems great, I don’t know. I just saw some Instagram, somebody there taking some great photos of the Eiffel Tower. I would love to go to Paris, so you decide, okay, Paris is the play. And then second, well, when is a good time to go to Paris? When do we have off? Oh, we could go in the middle of August, we’ve got some time off work then, let’s choose… How about August 15th to 22nd? That’d be perfect to go to… Okay, so we’re gonna go to in Paris, August 15th to 22nd. Step three, let’s look at what the air fare costs and by already choosing the destination and already choosing the dates and then going to search for the fares, the end result most of the time is pretty expensive flights, and then we’re left wondering, well, why the heck are flights always so damn expensive.

And so instead, what I recommend folks is, if you wanna get cheap flights, if cheap flights are really a priority, don’t make them the last priority in the way that you did in this three-step approach of the destination-first approach. Instead, make it the top priority, take that same three-step process and flip it on its head. Step one, this is what I call the flight-first approach, step one, where are their cheap flights available from my home airport right now? So let’s say you live in Los Angeles just in the past week, there were flights from LAX to Hawaii for $160 round trip, there were flights for LAX down to Costa Rica for I believe $240 round trip or over to Barcelona for $385 round trip. Oh man, I would love to go to Hawaii. All of those sound great, but Hawaii seems really, really awesome. So then step two, you decide of those places where they’re cheap, which one interests me the most, chose Hawaii of those three. Step three, what dates work for my schedule that have those cheap fares available? Oh, we could go August 17th through 24th. I see there’s $160 fares available, then let’s do it that way.

And so it’s the same three steps, but just by re-ordering it and putting cheap flights as the top priority rather than the last priority, that’s how you end up being able to catch cheap light and being able to take three or four vacations for the same price you use to pay for one. I think the mistake a lot of folks make is getting their heart set on one destination at the expense of all their options, when in reality, I think most people would… Are like me, they love to see most places in the world, and it’s just a matter of when to go visit them, and I like to use cheap flights as kind of the determinant there. If there’s a cheap flight available right now to Hawaii, great, I’m gonna hop on that even if it’s for three, six months from now, knowing that Paris isn’t going anywhere, it’ll still be there next time we show up. I think a lot of folks approach travel planning and flight searching as though they’re showing up at a restaurant. And the waiter offers them the menu and they just wave it away and say, “No, no, no, I’m gonna have the filet mignon, please.”

Don’t even look at the price and then get a little surprised when the bill comes and they just bought the most expensive dinner that they’ve had in a month. Instead I like to look for those bargains, look for those values, and remembering that the availability of cheap flights is not something that stays static, it’s not that there’s one price from LA to Paris, maybe it’s expensive right now, so I’m gonna book somewhere else, but maybe later this year it ends up popping up pretty cheap and I can take advantage of it then.

Brett McKay: What I love about this technique too, is that it injects some serendipity in your life, ’cause you see, “Oh, I never would have bought of going to Costa Rica, but it’s only $150.” I’ll go do that.

Scott Keyes: That’s exactly right. Look, that trip to Milan, that $130 flight that I took, I woke up that morning with zero intention of booking a flight to Italy that day. It was not something that was on my mind at all. I am not a fashionable person, if you saw me right now, I am in shorts and a T-shirt and looking a little bit slovenly frankly, to go to such a fashion-forward place. But for $130 round trip, there’s basically nowhere in the world that I wouldn’t go. And then once I get there realizing, oh, there are all these kind of hidden gems in the area. I popped up to Lake Como, went to hike in Cinque Terre, went skiing in the Alps, went to a AC Milan Champions League game. It was so much fun in a way that again, totally serendipitous rather than if I had sort of pre-scripted everything from the get-go and kind of looked at a map and decided, “Okay, I’m going here,” and then just hoping and praying that cheap fares pop up and by again putting that price is the top priority, it left my wallet still so flushed that I could be doing it again a few months from then and continuing to take more and more trips each year.

Brett McKay: Okay. So the first technique, I think it’s paradigm-shifting for a lot of people, look for the flight first, look for the cheapest flight first, and then pick your destination. But let’s say someone needs to take a destination-first approach to finding a flight, like said they’ve got a wedding they gotta go to, for example, what are some things you can do to still find cheap flights even though you’ve got a destination in mind first?

Scott Keyes: That’s right, look, flexibility is the single most important thing you can do for yourself to get cheap flights, but it’s not the… You don’t always have a ton of flexibility in every trip, sometimes you’ve got that wedding where you don’t have control over the destination, you don’t have control over the dates, and you’d still like to make sure that you are not paying an arm and a leg to afford those flights. And so even in those situations, you still have a lot of control over making sure you get the best deal possible. The single most important thing you can do for those trips where you don’t have much flexibility is to get the timing of your booking right. I use this technique called the Goldilocks Windows approach. So what this idea is, is that there are certain windows in advance of purchase when cheap flights are most likely to pop up. If you’re traveling domestically, it’s usually about one to three months in advances when a cheap flight is most likely to pop up, if you’re traveling internationally, about two to eight months, it’s a much larger window when those cheap flights are most likely to pop up, and if you’re traveling during a peak travel period, middle of summer or Christmas, New Year or something like that, you need to add a few months to those recommendations.

So advanced planning is especially critical if you don’t have any flexibility about where or when you go. But even then, trying to make sure that you are not only getting the timing of your booking right, but that you’re taking advantage of any other little nudges that can help get you a cheaper flight. Are you willing to add or subtract a day to your trip if fares are significantly cheaper? Let’s say you live in Philadelphia, are you willing to keep an eye on cheap flights out of Newark or out of BWI or Washington DC if fares are significantly cheaper than out of Philly. Are you willing to… Making sure you check southwest.com separately because their fares don’t show up on flight search engines. There are a lot of little tips and tricks like that to make sure that you’re still getting the best deal possible even in those instances where you have much less flexibility than a normal vacation.

Brett McKay: Yeah, I love the example of being intentional about the airport you fly out of. That can just knock… In one case, I think it was an international flight, it knocked thousands of dollars of a plane ticket. Someone took a three-hour drive to a different airport.

Scott Keyes: Yeah. This is one of my favorites… This is one of my favorite stories. So one of the people I interviewed for my book, Take More Vacations, was Shanna Lathwell, and she and her… She has a family of five, they live outside Detroit, Michigan, so Detroit’s their home airport. She had always wanted to take her family out to Bali, but flights from Detroit to Bali are normally $2500 somewhere in that ballpark. And so a family of five, we’re talking $12,500 just for the flights. And so that was of course, totally out of the question, but all of a sudden, one day she got an alert from Scacchi flights that fares to Bali had popped up for $550 out of Chicago. Now, what was interesting was Chicago’s obviously not her home airport, but she could buy five tickets for a flight out of Chicago to Bali for the same price that it would cost for one ticket out of Detroit to Bali. And so the question then was, is it worth… Is Detroit more convenient to fly out of than Chicago, but is it $10,000 more convenient? And that’s a pretty easy question especially for a family of five.

So what they did was just they bought those five tickets from Chicago to Bali, they hopped in the car, they drove the three or four hours, whatever it is, to drive from Detroit to Chicago and caught the flight there, and the funny thing about it was because it’s a much simpler itinerary from Chicago, it was just a… I believe it was Chicago to Taipei then down to Bali with a pretty brief layover. It was actually going to be shorter travel time total even with the drive over to Chicago than if they were to book a flight out of Detroit that had two connections, long layovers. The way I put it is like, if she had… If she and some friends had booked their flights and their friends were flying out of Detroit and she was flying out of Chicago, even with the drive over, she would have gotten there three or four hours earlier, been able to get lunch, take some surf lessons, hang out at the pool, waiting for their friends flying out of Detroit to get to Bali and meet them. So not only can it sometimes save you a ton of money to keep an eye on nearby airports, it can even sometimes actually save you time as well.

Brett McKay: So I think if you don’t have any flexibility on your destination or the time, I guess the trick is to find ways to inject flexibility in your travel plans, whether that’s changing the airport you fly out of, or maybe even the airport you fly into, and you have to maybe drive a few hours or be flexible when you fly in. So maybe you get there a little bit earlier ’cause the ticket is a little bit cheaper, or you leave a little bit later.

Scott Keyes: That’s right. Look, I took a trip once to Norway, I was flying out of Washington DC. Flights from DC to Norway at the time were $700, $800. It wasn’t cheap, but what I ended up stumbling across was a flight from DC to Brussels in Belgium for $225 round trip. Once I got to Brussels, being able to catch a budget flight up to Oslo was $50. And so by pairing a cheap flight across the Atlantic with then a cheap flight within Europe, I was able to save $400, $500 off what it would have cost to book it as a single itinerary from DC to Oslo. What was especially great about splitting up that way, it wasn’t just the money savings, and then also that I could take some time to explore Brussels before my flight up to Oslo and so I spaced it out by a day or two, got to basically get a free layover in Belgium, hang out, have some good waffles, some great fries, see the weird Manneken Pis statue. It was awesome. It was the… Like 48 hours was the perfect amount of time to spend on that trip and then continue on to my final destination, so yeah, giving…

I think a lot of times people unintentionally knee-cap themselves by thinking of flexibility as a binary, either you’re totally flexible or you have zero flexibility, when in reality, it’s much more of a spectrum, it’s much more of a dimmer switch. You have some amount of flexibility in trying to take advantage of it where you can, to get cheaper flights with without having to always have the 100% flexibility that maybe you did as a solo travel in your early 20s, taking a vacation.

Brett McKay: Okay, and so to reiterate too, there’s the Goldilocks model for when you wanna buy a ticket, and that’s one month to three months out for most flights. It’s gonna be a little bit longer if you’re trying to plan a flight at peak flight season and for a bunch of complicated reasons you talk about in the book, and this… I thought this was really interesting. Flights usually aren’t cheaper if you book them more than three months out, and then you don’t also don’t wanna wait the last minute because airlines are counting on business travelers who they don’t care about the price because the company is paying for it and they gotta make it to a meeting regardless. So they’re counting on them to buy the last-minute tickets, so it’s always gonna be really expensive last minute. So I guess take away, follow the Goldilocks model one or three months out, buy your ticket. And then as you mentioned, I think some people think if you book your flight on this day or on a certain day, you’re gonna find the cheapest flights, and you said that used to be the case a long time ago, but that’s not the case anymore.

Scott Keyes: Yeah, this is one of those misconceptions where 20 years ago, when airlines first started selling their tickets online, they really would load their fares once a week at a pre-determined time, like say, Tuesday at 1:00 PM, and if you are one of the first people to book flights after that happened, you really could get some… They had a very limited number of cheap flights and you could really take advantage. The problem is that that is not how airlines have priced their tickets for years now, nowadays airfare is set algorithmically, it’s changing by the day, if not by the hour, and so while there’s no pre-determined time when the flights are cheapest to book, there are cheaper days generally to fly. We talked about the business travelers versus leisure travelers, the cheapest days to fly are typically Tuesday, Wednesday and Saturday, those are more often than not going to be cheaper. It’s not 100% of the time. I like to think of it kind of as something of a betting line, look, when LeBron steps on a basketball court, he’s usually favored to win, but that doesn’t mean he’s never lost a game. It’s kind of the same with cheapest days of the week to fly, usually those are gonna be cheaper, but sometimes you’ll see cheap flights pop up on Mondays or Sundays or Fridays, it’s just a little bit less likely.

Brett McKay: And what about the seasonality around prices? ’cause I’m sure summer time is probably the most expensive time to fly, but are there periods to fly when it’s cheaper? ‘Cause I know in the book you talk about how flying Thanksgiving week in the United States is really expensive, but it can be the best with travel internationally, so are there any other periods like that to fly when it’s cheaper?

Scott Keyes: Absolutely. Look, summer and Christmas, New Years are the two most expensive times of year to fly. Summer is an expensive time of year to fly because you have all the students, teachers, families with kids in school who can only travel around the academic calendar. That sort of funneling of demand ends up leading to much more expensive tickets, whereas if you have the flexibility, if your schedule allows you to travel in the fall, in the winter, in the spring, you’re much more likely to see very, very cheap tickets during those times. The last thing too that I would note is that summer flights are always gonna be expensive, that seasonality, and the last minute summer flights are going to be especially expensive, and so I think a lot of the sticker shock that many folks are seeing right now is a little bit of that sort of confluence of factors working against people that not only are they looking for flights during the peak season, but they’re doing so at about the worst time to book that last minute window when fares tend to really skyrocket rather than come down in price.

Brett McKay: What’s your approach to searching for flights? Do you like Expedia, Kayak, Google Flights? What’s your process?

Scott Keyes: Yeah, they sort of open secret in the industries, they’re basically all the same, whether you search on Orbit, search on Expedia, search on Kayak, search on… My personal favorite is Google Flights. I just find it, the user interface, the user experience, to be significantly better, faster and more powerful, that’s why I like it, but the actual results that you’re going to see are going to be basically the same across the board.

So the good news is, if you have a preference one or the other, you really… You swear by Skyscanner, you love Kayak for it. It’s not gonna make a huge difference in the actual fares that you see, but what I would say is that you might wanna differentiate between where you search for your flights and where you book your flights, because the price tends to stay the same, to search for my flights on any one of those kind of meta-search sites where I’m comparing across airlines to making sure I’m getting the best price, but then when I actually go to the book, I typically like to book directly with the airline, and that’s for two reasons, one, because there are certain federal protections that you have when you book directly with the airline. For instance, there’s something called the 24-hour rule. This is a federal law that says when you book a flight directly with an airline, from the moment you hit purchase, you get a 24-hour grace period during which you can cancel your purchase and get a full cash refund, no questions asked. That is not the case under federal law when you book through an online travel agency. They might have their own policies or offerings on those, many of them do, but because they don’t have the weight of law behind them, they’re just not quite as attractive in my mind.

But second, when you book a flight directly with an airline, if something goes wrong with your itinerary, if the flight schedule gets changed, if there’s thunderstorms, if you decide to cancel or this or that, it’s much easier to handle or change your itinerary if you can just deal directly with the airline rather than having to deal with a middleman, because not only is a middle man gonna be more just an arduous process, but then you’ve got not only the airline’s policies, but the middleman’s policies to deal with as well, and so for simplicity sake, it ends up being far, far preferable if anything needs to change with your itinerary if you’ve booked directly with the airlines, so differentiating between where you search and where you book.

Brett McKay: Alright, so book with the airlines. And you talk about, you can take advantage of that 24-hour rule when you book with an airline. It’s a way to find better prices. It’s kind of arbitrage, right?

Scott Keyes: That’s right. So I’ll give you one example. There was a gentleman that I interviewed for the trip who had really wanted to travel to Japan. He was very, very excited to be able to visit, and when some cheap flights popped up for him, he was really excited to book them. I believe they were initially… I’m trying to find the exact price. Initially $572 he’d booked to them, but then within 24 hours, all of a sudden a better flight popped up, he was in DC, from Richmond to Tokyo for even cheaper, so he said, “Well, look, Richmond’s not that hard to get to. I’ll save the… Save $100, I’ll go down to Richmond and get a cheaper flight,” and because this new fare popped up within 24 hours, you could cancel the old itinerary and book the new ticket from Richmond to Tokyo. Well, then lo and behold again within 24 hours of doing that, another cheaper flight popped up, this time out of DC to Tokyo for just 584 bucks round trip, even better than the initial Richmond flight, so he cancelled that one, booked the new DC Tokyo flight for 584 and ended up being able to take a great trip, a much more convenient trip than what he had initially booked, and so the key to remember is that the 24-hour rule can help you in a few different ways. It can help you if you’re not 100% sure you wanna take a trip, but you see a really good fare.

So if you book it, what that does is essentially just freeze the price for 24 hours and give you time to decide, “Do you wanna keep this trip or would you rather just cancel and get your money back?” Maybe you need to consult with a significant other or a travel partner, but they’re in a meeting. Rather than risking the fare disappearing, which does happen, especially with really cheap fares, you could book it, lock it in for 24 hours and then cancel later if you decide you don’t want it. But then it also, the 24-hour rule, let you take advantage, like with this gentleman, Donald, and his flights to Tokyo, where if the price drops after you book, which happens more often than you would think. Airlines do you have what are called fare wars, where they’re essentially just ratcheting down the price to compete with one another. If there’s a fare war going on, you can book your flight, but then if the price gets cheaper or if it switches from a connecting flight to a non-stop flight, you can cancel your old itinerary, book the new one and take advantage without having to pay anything extra and in fact, be able to save the difference.

Brett McKay: And you also highlighted that you can do this with Southwest Airlines, use them as an arbitrage tool. So typically, Southwest, we think it’s a budget airline, right? But oftentimes, you can find better deal with the other airlines. So you’re saying, use Southwest Airlines to get to your initial destinations, you can lock in that kind of basically affordable price, but then keep looking for better deals with another airline.

Scott Keyes: Yeah, like… Okay, so I’ve got a wedding that I need to go to this September, and as soon as I got the dates for that wedding, what I did was went ahead on southwest.com and I just booked the best flight I could find with a reasonable price to the destination for those wedding dates. And the reason why I booked it on Southwest, and especially I did so with Southwest points that I had, is that Southwest flights are free to cancel. If you book with points, you just get all those points redeposited with no fear or anything. If you book with cash, they just hold your funds, the exact amount, as travel credit for a future trip.

And so what that does is it essentially lets you set a price ceiling, so in this instance, I believe I paid like $350 for the flight, and what that said was I set $350 as the maximum. So if the price went down on Southwest, well, I’ll just cancel and I’ll re-book it for the $300 price, if it does go down. If it goes up to $400, 450, no worries, I already got my $350 ticket. If it goes down on another airline, let’s say American offers that flight on those dates for 250, well, great, I’ll book that American flight, I’ll cancel my Southwest one for 350 and end up being able to take a cheaper trip. So either way, what it ends up allowing you to do, the Southwest arbitrage, is essentially create a heads, you win, tails, the airlines lose situation, and Lord knows we need more of those, because it feels like it’s more often the other case, that the airlines are usually the one to try to get one over on you, and so finding instances like this where you can say, “This is the most that I’m gonna pay,” and if there are any price drops between now and then, which they’re often are considering how volatile airfare is, you can take advantage and end up saving the difference.

Brett McKay: Another advanced tip you highlight that can save you a lot of money, especially if you’re flying international, and you mentioned this earlier, let’s say you wanna go some place in Europe, like Brussels, but it’s like direct flights from Brussels, from Chicago are crazy. But if you find a place to London that’s super cheap, basically, you said you can just build in a layover in London, and then as soon as you’re in Europe, it’s pretty cheap to fly anywhere in Europe after that point.

Scott Keyes: Yeah, that’s exactly right. So I call this the Greek island strategy, the idea that if you were to search for a flight from New York to Santorini, oftentimes they’re closer to like $1500, especially if you’re traveling in the summer, but flights from New York to Athens are regularly 450 bucks, and oftentimes non-stop, whereas there are no non-stops to Santorini from the US. Once you get to Athens, it’s really easy to hop a budget flight, hop a ferry, something else to get to the islands for 50 bucks, 75 bucks. And so not only do you end up being able to get a 66% price reduction off those $1500 Santorini flights, but you also, again, can build in that free layover where you can take as much time as you’d like in Athens before continuing on to Santorini and make it a free layover, free two in one trip.

Looking for… Especially when you are traveling, whether it’s somewhere remote or somewhere… Even just where there’s a… The destination, there aren’t many cheap flights popping up, getting… We talked about getting creative when you might not have full flexibility, keeping an eye on cheap nearby airports, knowing that once you get to Europe, once you get to Southeast Asia, it’s really easy to then continue on from the hub where you arrive to your final destination on another flight, and the reason why you need to take a little creativity and search this yourself is that the airlines themselves aren’t going to sell tickets on rival airlines, and so maybe the cheapest flight across the ocean, let’s just say it’s on British Airways, but then the cheapest flight from London down to Brussels is on… Let’s just say it’s on KLM. Let’s say you’re going to Amsterdam, it’s on KLM. You’re not going to be able to buy that as a single itinerary with British Airways and KLM because their rivals, they don’t sell one another’s tickets, and you’re not going to see a cheap, but instead, by buying one flight to London and a separate flight from London to Amsterdam, you are able to build yourself the cheapest itinerary, and so that’s why it’s important, especially when you have these long haul flights over an ocean, to see if you can do it cheaper by flying into a different gateway and then continuing on with a different airline to your final destination.

Brett McKay: Another tip to find cheap flights is mistake fares, and I guess you’re kinda hinting that you think that great deal you got to Milan was a mistake fare. What are those? And why do they happen? And how do you find them?

Scott Keyes: Oh, yeah. There was no question. That was a mistake fare. Mistake fares are interesting because they pop up more often than people would realize, and they end up getting honored much more often than people would think. Obviously that $130 flight got honored, but that’s not the only mistake fare I’ve gotten in my life. I’ve gotten a flight from the US to Japan for $169, round trip. Like half of my co-workers has got flights, got a business class, round trip flight to South East Asia for $550, round trip, a ticket that normally costs $5000 to Bangkok or Bali or Vietnam. And those types of deals pop up quite regularly, really eight, 10, 12 times a year, usually. Like I’m looking at one in just a couple of months ago, there were a mistake fare to Iceland, where it was Boston to Reykjavík for $100 round trip, DC to Reykjavík for 129, Denver to Reykjavík for 149 round trip. Those types of deals do pop up regularly. They pop up for a number of reasons. The classic case was like with that Milan deal where maybe they just accidentally forgot a zero at the end and sold it to me for $130 rather than $1300. There are other reasons why. Maybe the, again, air fare is set algorithmically nowadays, and so it’s much more difficult to often figure out will one change here produce a sort of anomaly in the end result of some other fares, and so they do pop up still pretty regularly.

The key when a mistake fare pops up is to book it as quickly as possible, again, taking advantage of the 24-hour rule, because as soon as they’re fixed, they’re gone. I remember looking at a flight once from the US to India, I believe it was from Dallas to India, for $212 round trip, and I was so excited, I was messaging friends, “Hey, who wants to take this trip?” By the time we sort of recruited a friend to go travel, we planned our itinerary and everything, we took two hours to plan where we were gonna go and when before then booking our flight, and I kid you not, 30 seconds before I went to book the flight, it disappeared, the $212 mistake was fixed, and so by dawdling, by taking our time, we ended up missing the deal.

Brett McKay: So you mentioned that prices right now are just crazy for summer travel. I guess your take is, if you really want to travel that place, it’s better to hold off if you want a cheaper flight?

Scott Keyes: Absolutely. Look, if you have the opportunity to travel in the fall or beyond, really Labor Day and beyond, fares are likely to be 50% lower or more. I mean, you see tons of… I think people have made the mistake of assuming that cheap flights are gone forever, when in reality, they’re just gone for this summer. We are still living in what I call the golden age of cheap flights. It’s just, at this point, as it would be in June of any summer, it’s virtually impossible to find cheap summer flights.

Brett McKay: Yeah, I think I read somewhere that flights are up by a third the summer. Is that right?

Scott Keyes: Yeah, they are significantly rebounded from where it was a year ago, still cheaper when you look up compared to where it was a decade ago, but small comfort for folks who kind of got used to those really cheap pandemic error flights and then are getting a bit of sticker shock this summer.

Brett McKay: Okay, so flights are really expensive in the summer any year, but they’re especially high this year because of pent-up travel demand during the pandemic, the airlines laid off pilots and they didn’t hire as many people, and now everyone wants to travel. But even if those things get smooth out, will prices go down in the fall like they usually do? Like will they go back to the normal fall levels that we’re used to, or things like inflation and oil price is gonna keep them from going back to the prices that were normally accustomed to?

Scott Keyes: They will go back. And you don’t have to take my word for it. You can just go look at the prices for the fall right now. I took a look before chatting with you, and just a couple of sample fares. For instance, if you wanted to fly right now from Chicago to Cancun, July 21st through 29th, 583. September 21st through 29th, 233. Austin down to Aruba, July 8th through 15th, 951 round trip. November 8th through 15th, 293 round trip. If your schedule allows you to travel in the fall or the winter, you really can take advantage of a lot of the cheap flights that are still available, but you wanna try to book those sooner rather than later. If you wait, again, to the last minute to book those, if you may till September to book your flight in October, it could be kind of difficult to get something cheap, whereas if you try to get those on the books now and give your today’s self something to look forward to, it’s going to end up being better both for your happiness and for your wallet.

Brett McKay: So you guys, big takeaway there, if you’re gonna plan a trip, plan for the fall. And even if prices do go up a little bit, they’re still good deals to be found.

Scott Keyes: Absolutely, absolutely. Look, if your schedule allows it, try to avoid, frankly, flying in the middle of summer. That’s when fares are going to be most expensive. If cheap flights are important to you, traveling in the middle of summer is generally not going to be the best time to do that. But even if you really wanna travel in summer and you really wanna still get a good deal, having to plan well ahead… What I like to say is, if you wanna travel peak season, always book opposite season. In the same way that swim suits are gonna be cheapest to buy in the winter, same with your summer flights, purchasing those in the winter, and so what that means is right now, in the summer, the cheapest thing to buy in stores are those winter coats. The cheapest flights to buy right now are those winter holiday flights, so think about booking your Christmas, New Year’s flights now, where they’re gonna be much cheaper than if you wait four or five months and are trying to book them at the same time as everybody else and seeing really expense fares at that point.

Brett McKay: Well, Scott, it’s been a great conversation. Where can people go to learn more about the book and your work?

Scott Keyes: Absolutely. So the book is available at any book store, some of the large conglomerate selling books online or your local independent book store. It’s called Take More Vacations. And you can sign up for alerts about cheap light popping up from your home airport at scottscheapflights.com, no apostrophes, no underscores. That’s scottscheapflights.com.

Brett McKay: Fantastic. Well, Scott Keyes, thanks for your time. It’s been a pleasure.

Scott Keyes: My pleasure, Brett. Thank you so much for having me.

Brett McKay: My guest there was Scott Keyes. He’s the founder of Scott’s Cheap Flights. You can check that out. It’s scottscheapflights.com. Also check out his book, Take More Vacations, available on Amazon.com and book stores everywhere. Also check out our shownotes at aom.is/cheapflights, where you can find links to resources, we delve deeper into this topic.

Well, that wraps up another edition of The AOM Podcast. Make sure to check out our website at artofmanliness.com, where you can find our podcast archives, as well as thousands of articles written over the years about pretty much anything you think of. And if you’d like to enjoy ad-free episodes of The AOM podcast, you can do so on Stitcher Premium. Head over to stitcherpremium.com, sign up, use code Manliness to check out for a free month trial. Once you’re signed up, download the Stitcher app on Android, IOS and you can start enjoying ad-free episodes of The AOM podcast. And if you haven’t done so already, I’d appreciate if you take one minute to give us a review on Apple Podcast or Spotify. It helps out a lot. And if you’ve done that already, thank you. Please consider sharing the show with a friend or family member who you think would get something out of it. As always, thanks for the continued support. Until next time, it’s Brett McKay. Reminding you to not only listen to the AOM podcast, but put what you’ve heard into action.