The Secrets to Booking Cheap Flights
Episode Stats
Summary
Scott Kiese is the founder of Scott's Cheap Flights and the author of Take More Vacations: How to Search Better, Book Cheaper, and Travel the World. In this episode, 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. He also explains how to use the 24-hour rule and Southwest Airlines as arbitrage and get better prices on your tickets.
Transcript
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brett mckay here and welcome to another edition of the art of manliness podcast travel can offer
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a lot of good memory making adventure mind expanding experiences and plenty of fun and
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relaxation it's not surprising then that most people say they'd like to travel more than they
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do what's keeping them from fulfilling that desire well one obstacle especially these days
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is that the high price of plane tickets puts flying out of reach my guest today can help you
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surmount this obstacle so you can get away more often his name is scott kyes he's the founder of
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scott's cheap flights and the author of take more vacations how to search better book cheaper and
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travel the world today on the show scott shares how scoring cheap flights can help you travel more
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often the advantages of taking more frequent vacations and the psychological benefit of
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planning your trips well in advance we then get into the misconceptions people have about ticket
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pricing from there we turn to scott's strategies for booking cheap flights beginning with why he
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recommends adopting a flight first rather than destination first approach scott shares the
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goldilocks time window when cheap flights are most likely to pop up the benefits of building
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flexibility into your itinerary the days that are typically cheapest to fly and his favorite search
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site to look for flights he also explains how to use the 24 hour rule and southwest airlines as
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arbitrage and getting better prices on your tickets and how to employ what he calls the greek
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island strategy to save more money when flying internationally we end our conversation with how to take
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advantage of mistake fares and whether the high prices you're seeing the summer are here to stay
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after the show's over check out our show notes at awem.is slash cheap flights
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all right scott kyes welcome to the show thank you so much for having me i'm excited to be here
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so you are the founder of scott's cheap flights where you highlight cheap flights that are out there
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you've become the guru at finding really cheap flights you got a new book out where you highlight
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all the tips you've learned over the years of finding cheap flights how did this happen how did
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you end up becoming the cheap flights guru well it started off when i went to school and studied cheap
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flights i got my degree you know in cheap flight ology and no no no i i actually this was all a very
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serendipitous occurrence for me i never in my life would have imagined that i would become
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an entrepreneur much less a cheap flight entrepreneur i studied writing and political science in college
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i was a journalist for a while in a previous life and i really kind of happened backwards into this
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life where you know they say that necessity is the mother of invention well i was somebody who out of
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college had huge dreams of wanting to travel to europe and asia and elsewhere but basically no money
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to do it and so i knew somehow people were out there getting cheap flights but at the time i had
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no idea how they were doing it and every time i was searching for flights it was like they all were
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expensive you know unaffordable how how were people doing this and so what i ended up doing was really
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kind of putting on that journalist hat and scratching that itch of why is it that airfare is so volatile
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how do you put yourself in a position to get those cheap flights when they pop up and this all then
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culminated a year or two later when i got what is still to this day probably the single best deal that
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i've ever personally gotten and that was non-stop from new york city to milan for 130 round trip
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this was a steal there's probably a flight that they meant to sell for 1300 and forgot a zero at the end
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but when i booked it it was 130 and it was probably the best deal i've ever gotten and so by taking this
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this wonderful trip to northern italy and going skiing in the alps and hiking in cinque terra not
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only did i end up having this wonderful incredible trip but when i got back all my i guess word had
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spread to all my friends and co-workers and they kept coming up to me hey scott you know i heard about
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that great deal you got uh listen next time you find a deal like that can you let me know so i can get
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in on it too and so rather than trying to remember every single person i needed to let know next time
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i found a deal i decided well why don't i just make a simple little email list and this way i can let
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everybody know at the same time in that moment scott's cheap flights was born but i had no idea
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because i wasn't an aspiring entrepreneur at the time i was just somebody who wanted to solve this
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problem of letting everybody know when i found cheap flights and but then over the next year or two it
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grew and grew until it was finally time to to think about turning it into an actual business
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and here we are today talking to you about cheap flights exactly look everybody else says they have
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the coolest job in the world but i get to find cheap flights every single day and help people take
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make their vacation dreams come true so i i would at least like to put my hat in the ring for that one
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so you're helping people find cheap flights not for the sake of finding cheap flights like you're
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really passionate about this because you want people to take more vacations in fact that's what
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the title of your latest book is called take more vacations let's talk about that like why do you
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think people particularly americans need to take more vacation like what is the state of vacationing
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for americans so there are a few reasons why first reason why is because everybody says they want to
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everybody says you know traveling and taking more vacation it's one of the top new year's resolutions
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every year it's one of the top and when you look at survey data of what people want to do when they
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retire it's always up there number one number two everybody desires to take more vacations than they
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actually do when you look at the data on how many vacation days people have actually been taking
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it's basically been on a downward slide for the past 25 years you know in the late 90s people were
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taking on average 21 days of vacation a year and the most recent data was more like 17 days 16 days
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and for millennials it was under 15 days per year of vacation and so everybody wants to take more
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and yet we're taking less and less and so part of it was to figure out well why is that the case why
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isn't our actions lining up with our desires and one of the things that i really was struck by is how
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much the stress and complexity of trying to book flights is weighing on people's ability to take
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vacations that because airfare is the single most volatile thing that most people purchase
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that ends up leading to a ton of stress it you know it's planning is paradoxically both the most
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enjoyable part of a trip but also the most stressful part for most people and i think that's actually
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causing people to take fewer vacations than they would otherwise because they seem to only see expensive
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flights because they don't know if i don't you know if i see this fair today should i book it will
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it go up tomorrow will it go down how about a month from now it ends up just leaving people much more
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anxious about an activity that is theoretically supposed to be one that's supposed to take their anxieties
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away and so partially it's just trying to do this thing in service of what people say they want but
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really at the end of the day the reason why i think people ought to take more vacations is because i
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think you end up enjoying those vacations a lot more as a result people i think make a mistake of
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thinking of travel and thinking of vacation as just something that you go do to relax to you know sit on
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the beach and and take your cares away and that's that's fine there's nothing wrong with sipping a
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cocktail on the beach but i would argue that traveling and vacations are actually more like
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a muscle where the more you do it the better you get at matching the types of destinations the types
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of trips and the types of activities to your individual personality and so what i mean by that
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is when you look at people's satisfaction with their vacations over time it actually goes up as they
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take more vacations because they get better at figuring out will i enjoy a trip to you know the center
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of paris all the hustle and bustle or would i prefer something more in the countryside would i like to
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travel to somewhere where there's maybe a ton of pedestrian infrastructure where i can walk around
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or would i rather be somewhere where there is where it's very kind of nature focused there are tons of
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different types of trips out there that folks can take but it's difficult to figure out which one is
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right for you until you start to just take more of them and test it out and see what you what vibes
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most was the you rather than what vibes most was the average traveler and in finding cheap flights
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allows you to take more vacations i think most people you know because flights they think oh man
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they're so expensive i can only take one big vacation a year and because you only do it one time a year
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you're not able to find out like what do i really like and it also i think taking that one big vacation
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a year it puts a lot of pressure on that vacation like it has to if it's not out of the park you're
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going to be disappointed like man i just waste a lot of money and time but if you take smaller
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cheaper vacations you increase the chances of you having a better time yeah that was one of the
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biggest revelations for me on this 130 trip to milan was that because i got such a deal on the flight
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over the entire experience of the trip was so much different it was like this weight had been lifted off
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my shoulders where everything felt like it just had a halo to it it had some salt added i didn't have
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that pressure to enjoy myself and every single minute i could relax and and kind of take things
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a bit slower i could frankly spend a little bit more on you know i could get that truffle linguine i could
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buy that first class train ticket rather than sitting in coach i could you know splurge on the better
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seats for the ac milan soccer match like i could do these things because i had saved so much on the
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flight over there and so the cheaper the flight i think the better you time you end up having on the
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vacation itself because you can take that money you saved and devote it towards having a better trip but
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also because you don't have the same sort of pressure so i think it works both on a financial standpoint
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and as you mentioned on the sort of quantity of vacation standpoint if you take one big trip a
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year that's putting a lot of pressure on that trip to enjoy it making sure that this is you know all
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the sort of anticipation and pressure on this one trip and then you know maybe you get there and
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things don't go as planned maybe there's thunderstorms maybe you miss you know the boat or the flight or
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something you know i don't know you get you lose your wallet like things happen on travel where all of a
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sudden if it happens during this one trip that's your entire vacation budget time budget for the
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year whereas if you break that time up into two three four trips on the year not only is it much
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more spread out but then the hangover of coming out coming back home from your vacation is just a much
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different experience when you come back from that one big trip and it's 49 weeks until your next
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vacation buddy that is a tough tough outlook but if you come back and it's just three months
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until your next trip well that's totally doable you can already get busy planning planning out what
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you're going to do at three months from now on your next trip and so that's why i'm such an advocate
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of taking more vacations using cheap flights as a way to get them and then being able to not only
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enjoy yourself more on the trip but also being able to test out the places that you go
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further down the list you know if you have one trip a year you probably have to go to the big hits you
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go to paris and london and tokyo but if you have three or four trips a year you can take a chance you
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can take a flyer on going to albania to you know trinidad and tobago to taiwan places that are
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kind of further down the traditional list but might actually speak a lot to you personally and some of
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the best trips i've had have been those sort of b list c list places that are not at the top of the
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traditional tourist circuit but have been some of my favorite trips to trinidad and tobago to taiwan
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to lithuania that i'm so glad i was able to to see those places which i might not have if i only
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traveled once a year yes i feel like too when you go to the big the big hits you go there and you're
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like oh this looks like the pictures i've seen on the internet um it's kind of a letdown yeah yeah
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especially you know something like the eiffel tower the mona lisa like the tower of pisa exactly
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like i expected it to the tower of pisa it's leaning all right um so i also like too so there's
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all these uh you should hide like this research about when you take vacations it's great for your
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psychological health it's great for your physical health but you devoted this chapter about the
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anticipation factor of vacations so how in thinking about going on a vacation actually that's
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probably one of the most enjoyable parts but i mean talk about like what happens when you have
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something to look forward to that's right look i think a mistake that folks make when thinking
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about travel is we only think about travel as what happens on the trip itself you've got a seven day
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trip to costa rica and you just think about it during those seven days but if you actually look
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at the research of how people tend to enjoy their travels it turns out we actually get more happiness
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and more joy in the weeks and months leading up to a trip than we do on the trip itself
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and we actually get more joy in the weeks and months after a trip looking back on it than we
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did on the trip itself and that's not to say we don't enjoy the actual trip itself we do but we get
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even more happiness before and after a trip and i think a lot of folks maybe do themselves a disservice by
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buying into this idea of like oh romantic you know last minute getaway oh i'm just gonna book
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something for this weekend and go and that's fine there's nothing wrong with it i like being able to
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be spontaneous sometimes but i think that undercuts some of the ways that you can really enjoy your
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vacation by planning it further out and giving your today self the joy of that anticipation of looking
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forward to it you know the great thing about daydreams is nothing goes wrong in them when you're actually
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on that trip to costa rica i don't know you know maybe there's a thunderstorm maybe i don't know you get
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too close to some bad animal in the jungle your taxi driver like rips you off something like that
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but when you're a month out from that trip two months out and you're daydreaming about hiking through the
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jungle exploring the countryside going to those coffee farms and those beaches nothing is happening
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wrong in those in those daydreams and so that's why we tend to actually enjoy the anticipation of travel
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more than the trip itself and why i think that folks should be taking more effort to booking their
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travels further in advance and booking more of them so that way rather than just trying to book a trip
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a week before and then take it and then there's just hangover we've got nothing to look forward to
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for months on end instead book those trips three months out six months out i've basically always got a
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trip booked three or six months out so i have something to look forward to today that i can be
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excited about in the future all right so let's talk about how we can take more trips because plane
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tickets are usually the most expensive cost in a vacation especially now i'm sure people have tried
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to plan flights looking at it and they're just like oh my gosh like sticker shock it's like what's going on
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so let before we dig into how to find cheap flights i think it helped listeners to have a big picture
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overview of why plane ticket prices are so volatile i mean you check you can check one day and it's this
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price and then a few hours later it's like 10 times higher you check and you can see like an international
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flight is a cheaper flight than a domestic flight what's going on there why why are prices so all over
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the place yeah airfare is the most volatile thing that most people purchase and it's something that's
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really important to not fall prey to some of the classic mistakes that folks make of assuming that
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airfare is static a lot of folks will think well you know a flight from let's say new york to la is
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supposed to cost 300 when in reality it's a wide range that it's constantly swinging up and swinging
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down the reason why airfare is so volatile is it has a few unique characteristics to it that's unlike
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other things we purchase it is what's called a rival good when i buy a seat on a flight nobody else can
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buy that seat it you know if i get it nobody else gets it there's what's called spoilage so any unfilled
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seats when the door closes for that flight are spoiled they get no money for those so there's an
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expiration date and there's unpredictability of if or when travelers are actually going to book those
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flights and so airlines have to try to constantly be adjusting their price in anticipation that you
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know how many folks are going to book that flight to la if it's at three hundred dollars at three months
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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
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very sort of volatile set of circumstances and so the biggest thing that i think as consumers you can do
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is to stop thinking of airfare and flight tickets as something like a gallon of milk where we think of
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airfare you know when you think of a gallon of milk you go to the grocery store the price yesterday is
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going to be about the price today which is going to be about the price tomorrow and the price that you
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pay for a gallon of milk there is basically going to be contingent on how much milk you're actually
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getting you know a half gallon is going to be a little bit more than half the price of a full
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gallon etc but airfare is nothing like either of those to give you one example i remember looking
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once at a flight from atlanta to amsterdam this is a flight over memorial day i believe and on monday
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when we searched for it it was eight hundred dollars round trip on tuesday when we searched for the same
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flight it was three hundred dollars round trip and on wednesday when we searched for the same flight it
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was thirteen hundred dollars round trip and so it'll have the airfare will have these wild swings where
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it's not just like slowly creeping up and down it can change by you know orders of magnitude day by
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day and so that the best thing you can do as a consumer in many cases is to remember that today's
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expensive flight can be tomorrow's cheap flight and vice versa and when fares are expensive
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be patient when they're cheap pull the trigger quickly because that could change tomorrow and
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then the last thing i would say on this is you know we talked about how the price of milk is large
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to continue with how much you're buying airfare is not like that i remember looking at a flight last
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year from there were fares available from pittsburgh to to tokyo for 202 round trip this is an incredible
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fare obviously but uh do you know where else was available to fly from pittsburgh for 202 on the
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same dates philadelphia and so it was the exact same price for the exact same wildly wildly different
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amounts of flight distance and so getting it out of your head that oh the how far you fly has a direct
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relationship with how much you can expect to pay that's not the case with airfare i think a lot of my
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job is really trying to get folks to unlearn those mistakes or unlearn their sort of assumptions about
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what airfare is supposed to be any other common misconceptions you see either besides you know
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ticket price being correlated to trip distance any big other big ones you see that kind of mess people
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up oh goodness clearing your cookies incognito window people swear by this i mean if i cannot tell you
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how often i get you know yelled at to my face that i am absolutely wrong on this one that it totally
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matters you have to clear your cookies i went ahead and tested this once to see you know does it show a
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different fare the thinking being oh if the airlines can see you really you know you're searching for
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this flight then maybe they'll jack up the price to try to get as much money from you as possible so i
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went ahead and tested it once i searched a flight from denver to london october 6th through 13th and
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the fare came back as 442 round trip i searched a second time 442 round trip i took hours of my day
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to search this 100 times in a row and lo and behold on the 100th time just like the first time it was
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still 442 round trip i think the mistake people make is a sort of truman show-esque thing where where
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they see sometimes fares change when you are searching for them and that's because airfare like
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we've mentioned is extremely volatile but it's not because the airlines are watching you you know
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the individual brett searching for these flights and deciding oh we know we're going to jack up the
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price on them it's because airfare is always changing and in fact i think the logic is actually
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backwards in some ways because the way that most companies work is that if you engage in what's
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called an abandoned cart essentially you you know you're looking at a pair of pants from
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levi's you click on it but then you don't ultimately purchase it they see that you clicked
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on it they see that you didn't buy it their solution is not to jack up the price on those
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pants their solution instead is usually to hit you with a coupon code or some other way of discounting
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the price to try to get you to purchase in the first place so the good news it's not going to
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cause you to have more expensive flights to clear your cookies or to search in incognito
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it's just not necessary it's not going to make any difference whatsoever we're going to take a
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quick break for your word from our sponsors and now back to the show all right let's talk about
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some tactics to find cheap flights and you say most people when they search for a flight
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they use a destination first approach when finding flights but you argue that if you want to find the
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cheap flights you need to take a flight first approach so walk us through the difference between
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these two and how does a flight first approach help you find cheaper deals sure so let's say you know
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you're planning a typical vacation bread and and the way if you plan your vacation like most people
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you use what's called a destination first approach and so probably looks something like this tell me if
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i'm if i'm off base here you decide first where do you want to go oh you know the paris it's i've had
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it on my list for a while it seems great like i don't know i just saw some instagram somebody there
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taking some great photos of the eiffel tower i would love to go to paris so you decide okay paris
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is the play and then second well when is a good time to go to paris when do we have off oh we could
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go like in the middle of august you know we've got some time off work then let's choose how about
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august 15th through 22nd that'd be perfect to go to okay so we're going to go to paris august 15th
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22nd step three let's look at what the airfare costs and by already choosing the destination
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and already choosing the dates and then going to search for the fares the end result most of the
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time is pretty expensive flights and then we're left wondering well why the heck are flights always so
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damn expensive and so instead what i what i recommend folks is if you want to get cheap flights if cheap
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flights are really a priority don't make them the last priority in the in the way that you did in
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this three-step approach of the destination first approach instead make it the top priority take that
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same three-step process and flip it on its head step one this is what i call the flight first approach
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step one where are there cheap flights available from my home airport right now so let's say you live
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in los angeles just in the past week there were flights from lax to hawaii for 160 round trip
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there were flights for lax down to costa rica for i believe 240 round trip or over to barcelona for
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385 round trip oh man i would love to go to hawaii like all those sound great but hawaii seems really
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really awesome so on step two you decide of those places where they're cheap which one interests me the
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most chose hawaii of those three step three what dates work for my schedule that have those cheap
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fares available oh we could go august 17th through 24th i see this 160 fares available then let's do
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it that way and so it's the same three steps but just by reordering it and putting cheap flights as
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the top priority rather than the last priority that's how you end up being able to get cheap flights and
00:24:54.640
being able to take three or four vacations for the same price you used to pay for one i think the mistake
00:25:01.280
a lot of folks make is getting their heart set on one destination at the expense of all their options
00:25:08.380
when in reality i think most people would are like me they'd love to see most places in the world and
00:25:15.080
you know it's just a matter of when to go visit them and i like to use cheap flights as kind of the
00:25:20.400
determinant there like if there's a cheap flight available right now to hawaii great i'm gonna hop
00:25:25.120
on that even if it's for three six months from now knowing that paris isn't going anywhere it'll still
00:25:30.960
be there next time we show up you know i think i think a lot of folks approach travel planning and
00:25:37.280
flight searching as though they're showing up at a restaurant and you know the waiter offers them the
00:25:43.100
menu and they just wave it away and say no no no i'm gonna have the filet mignon please don't even look
00:25:48.040
at the price and then you know get a little surprised when the bill comes and and they just
00:25:52.780
bought the most expensive dinner that they've had in a month instead you know i like to look for those
00:25:58.240
bargains look for those values and remembering that the availability of cheap flights is not something
00:26:04.000
that stays static it's not that there's one price from la to paris maybe it's expensive right now so
00:26:10.340
i'm going to book somewhere else but maybe later this year it ends up popping up pretty cheap and i can
00:26:15.020
take advantage of it then no i love about this technique too is that it injects some serendipity
00:26:19.960
in your life right because you see oh i never would have thought of going to costa rica but it's
00:26:23.640
only 150 bucks i'll go do that that that's exactly right look that trip to milan that 130 flight that i
00:26:30.020
took i woke up that morning with zero intention of booking a flight to italy that day it was not
00:26:36.420
something that was on my mind at all i am not a fashionable person if you saw me right now i am in shorts
00:26:42.880
and a t-shirt and looking a little bit slovenly frankly to go to such a you know fashion forward
00:26:48.440
place but for 130 round trip i mean there's basically nowhere in the world that i wouldn't go
00:26:54.420
and then once i get there realizing oh there are all these like kind of hidden gems in the area oh i
00:26:59.980
could popped up to lake como went to hike in cinque terra went skiing in the alps went to a ac milan
00:27:05.400
you know champions league game it was so much fun in a way that again totally serendipitous that rather
00:27:12.680
than if i had sort of prescripted everything from the get-go and kind of looked at a map and decided
00:27:18.160
okay i'm going here and then just hoping and praying that cheap fares pop up and by again putting
00:27:23.740
that that price as the top priority it left my wallet still so flush that i could be take doing it again
00:27:30.940
you know a few months from then and continuing to take more and more trips each year okay so the
00:27:37.300
first technique i think it's paradigm shifting for a lot of people look for the flight first look for
00:27:42.360
the cheapest flight first and then pick your destination but let's say someone needs to take
00:27:46.680
a destination first approach to finding a flight like say they've got a wedding they got to go to
00:27:51.440
for example what what are some things you can do to still find cheap flights even though you've got
00:27:57.700
a destination in mind first that's right look flexibility is the single most important thing
00:28:03.080
you can do for yourself to get cheap flights but it's not the only you know you don't have always
00:28:08.740
have a ton of flexibility in every trip sometimes you've got that wedding where you don't have
00:28:13.720
control over the destination you don't have control over the dates and you'd still like to make sure
00:28:18.620
that you you know are not paying an arm and a leg to for those flights and so even in those
00:28:24.300
situations you still have a lot of control over making sure you get the best deal possible the
00:28:30.340
single most important thing you can do for those trips where you don't have much flexibility is to
00:28:36.040
get the timing of your booking right i use this technique called the goldilocks windows approach
00:28:42.380
so what this idea is is that there are certain windows in advance of purchase when cheap flights are
00:28:49.900
most likely to pop up if you're traveling domestically it's usually about one to three
00:28:55.560
months in advance is when a cheap flight is most likely to pop up if you're traveling internationally
00:29:00.980
about two to eight months it's a much larger window when those cheap flights are most likely to pop up
00:29:05.980
and if you're traveling during a peak travel period you know middle of summer christmas new year
00:29:11.040
something like that you need to add a few months to those recommendations so advanced planning is is
00:29:16.500
especially critical if you don't have any flexibility about where or when you go but even
00:29:23.480
then you know trying to make sure that you are not only getting the timing of your booking right but
00:29:30.220
that you're taking advantage of any other like little kind of nudges that can help get you a cheaper
00:29:35.560
flight so maybe you know are you willing to add or subtract a day to your trip if fares are significantly
00:29:42.000
cheaper let's say you live in philadelphia are you willing to you know keep an eye on cheap flights
00:29:48.020
out of newark or out of bwi or you know washington dc if fares are significantly cheaper than out of
00:29:54.620
philly are you willing to you know making sure you check southwest.com separately because their fares don't
00:30:00.920
show up on flight search engines there are a lot of kind of little tips and tricks like that to make sure
00:30:07.180
that you're still getting the best deal possible even in those instances where you have much less
00:30:12.520
flexibility than a normal vacation yeah i love the example of you know being intentional about the
00:30:18.700
airport you fly out because that can that can just knock i mean in one case i think it was an
00:30:22.420
international flight it knocked like thousands of dollars off of a plane ticket because someone took
00:30:26.660
a three-hour drive to a different airport yeah this is one of my favorite this is one of my favorite
00:30:32.180
stories so one of the people i interviewed for my book take more vacations was shanna
00:30:36.120
laugh well and she and her she has a family of five they live outside detroit michigan so detroit's
00:30:41.220
their home airport she had always wanted to take her family out out to bali but flights from detroit to
00:30:48.220
bali are normally like twenty five hundred dollars you know somewhere in that in that ballpark and so
00:30:54.220
family of five we're talking twelve thousand five hundred dollars just for the flights and so that was
00:31:00.980
of course like totally out of the question but all of a sudden one day she got an alert
00:31:05.760
from scott street flights that fares to bali had popped up for 550 out of chicago now what was
00:31:14.240
interesting was chicago is obviously not her home airport but she could buy five tickets for a flight
00:31:21.520
out of chicago to bali for the same price that it would cost for one ticket out of detroit to bali and
00:31:28.280
so the question then was is it worth it like it's not is detroit more convenient to fly out of
00:31:35.240
than chicago but is it ten thousand dollars more convenient and that's a pretty like that's a
00:31:42.720
pretty easy question especially for a family of five so what they did was just they bought those five
00:31:48.040
tickets from chicago to bali they hopped in the car they drove the you know three or four hours whatever
00:31:54.420
it is to drive from detroit to chicago and caught the flight there and the funny thing about it was
00:32:00.440
because it it's a much simpler itinerary from chicago it's just a believe it was chicago to
00:32:07.700
taipei then down to bali with a pretty brief layover it was actually going to be shorter travel time
00:32:14.820
total even with the drive over to chicago than if they were to book a flight out of detroit that had
00:32:21.020
two connections long layovers the way i put it is like you if she had if she and some friends had booked
00:32:28.420
their flights and their friends were flying out of detroit and she was flying out of chicago even
00:32:32.340
with the drive over she would have gotten there three or four hours earlier been able to you know
00:32:36.880
get lunch take some surf lessons hang out at the pool waiting for their friends flying out of detroit
00:32:43.200
to actually get to bali and meet them so not only can it sometimes save you a ton of money to keep an
00:32:48.940
eye on nearby airports it can even sometimes actually save you time as well okay so i think if you don't have
00:32:55.060
any flexibility on your destination or the time i guess the trick is find ways to inject flexibility
00:33:00.840
in your travel plans whether that's changing the airport you fly out of or maybe even the airport
00:33:05.140
you fly into and you have to maybe drive a few hours or be flexible and you know when you fly in so
00:33:11.720
maybe if you get there a little bit earlier because the tickets a little bit cheaper or you leave a little
00:33:16.760
bit later that's right look i took a trip once to norway i was flying out of out of washington dc
00:33:23.700
flights from dc to norway at the time were you know 700 800 bucks like it wasn't cheap but what i ended
00:33:32.160
up stumbling across was a flight from dc to brussels in belgium for 225 round trip once i got to brussels
00:33:41.220
being able to catch a you know budget flight up to oslo was like 50 and so by pairing a cheap flight
00:33:49.200
across the atlantic within a cheap flight within europe i was able to save four or five hundred
00:33:55.360
dollars off what it would have cost to book it as a single itinerary from dc to oslo what was
00:34:01.580
especially great about splitting up that way wasn't just the money savings and then also that i could
00:34:07.100
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
00:34:15.160
basically get a free layover in belgium hang out you know have some good waffles some great fries you
00:34:20.620
know see the the weird mannequin piss statue like it was it was awesome it was the you know i didn't
00:34:26.320
like 48 hours was the perfect amount of time to to spend on that trip and then continue on to my final
00:34:32.240
destination so again yeah giving your i think a lot of times people unintentionally kneecap themselves by
00:34:39.740
thinking of flexibility as a binary either you're totally flexible or you have zero flexibility
00:34:44.880
when in reality it's much more of a spectrum it's much more of a dimmer switch you have some amount
00:34:50.220
of flexibility and trying to take advantage of it where you can to get cheaper flights without having
00:34:55.760
to without having to always have like a hundred 100 flexibility that maybe you did as a solo traveler
00:35:03.460
in your early 20s taking a vacation okay and so to reiterate too there's the goldilocks model
00:35:09.120
for when you want to buy a ticket and that's like you know one month to three months out for most
00:35:13.660
flights it's going to be a little bit longer if you're trying to plan a flight at peak flight season
00:35:18.800
and for a bunch of complicated reasons you talk about in the book and this i thought this was really
00:35:22.440
interesting flights usually aren't cheaper if you book them more than three months out and then you
00:35:28.900
don't also don't want to wait the last minute because airlines are counting on business travelers who
00:35:33.380
they don't care about the price because you know the company's paying for it and they got to make it to a
00:35:37.840
meeting regardless so they're counting on them to buy the last minute tickets so it's always going
00:35:43.340
to be really expensive last minute so i guess take away follow the goldilocks model one to three months
00:35:48.320
out buy your ticket and then as you mentioned i think some people think if you book your flight you
00:35:53.380
know on this day or on a certain day you're going to find the cheapest flights and you said that used
00:35:58.620
to be the case you know a long time ago but that's not the case anymore yeah this is one of those
00:36:03.640
misconceptions where 20 years ago when airlines first started selling their tickets online they
00:36:09.120
really would load their fares once a week at a predetermined time like say tuesday at 1 p.m
00:36:14.420
and if you were one of the first people to book flights after that happened you really could get
00:36:19.440
some you know they had a very limited number of cheap flights and you could really take advantage
00:36:23.020
the problem is that that is not how airlines have priced their tickets for years now nowadays airfare
00:36:29.640
is set algorithmically it's changing by the day if not by the hour and so while there's no
00:36:35.940
predetermined time when flights are cheapest to book there are cheaper days generally to fly you know
00:36:43.460
we talked about the business travelers versus leisure travelers the cheapest days to fly are typically
00:36:48.920
tuesday wednesday and saturday those are more often than not going to be cheaper it's not a hundred
00:36:55.460
percent of the time i like to think of it kind of as a as a something of a betting line look when
00:37:00.740
lebron steps on a basketball court he's usually favored to win but that doesn't mean he's never
00:37:05.220
lost a game it's kind of the same with cheapest days of the week to fly they're usually those are
00:37:11.520
going to be cheaper but sometimes you'll see cheap flights pop up on mondays or sundays or or fridays
00:37:16.600
it's just a little bit less likely and what about the seasonality around prices because i mean i'm sure
00:37:21.680
okay summertime is probably the most expensive time to fly but are there periods to fly when it's
00:37:26.440
cheaper because i know you know in the book you talk about how flying thanksgiving week in the united
00:37:30.960
states is really expensive but it can be the best week to travel internationally so i mean are there
00:37:37.200
any other periods like that to fly when it's cheaper absolutely look summer and and christmas new
00:37:42.880
years are the two most expensive times of year to fly summer is an expensive time of year to fly
00:37:48.620
because you have all the you know students teachers families with kids in school who can
00:37:54.000
only travel around the academic calendar that sort of funneling of demand ends up leading to much more
00:38:00.260
expensive tickets whereas if you have the flexibility if your schedule allows you to travel in the fall
00:38:07.320
in the winter in the spring you're much more likely to see very very cheap tickets during those times
00:38:14.560
the last thing too that i would note is that summer flights are always going to be expensive that
00:38:20.000
seasonality and last minute summer flights are going to be especially expensive and so i think a lot of
00:38:26.400
the sticker shock that many folks are seeing right now is a little bit of that sort of confluence of
00:38:33.380
of factors working against people that not only are they looking for flights during the peak season but
00:38:39.460
they're doing so at about the worst time to book that last minute window when fares tend to really
00:38:45.200
skyrocket rather than come down in price what's your approach to searching for flights do you like
00:38:50.800
expedia kayak google flights what's your process yeah they they sort of open secret in the industries
00:38:57.320
they're basically all the same whether you search on orbit search on expedia search on kayak search on
00:39:03.240
my personal favorite is google flights i just find it the user interface the user experience to be
00:39:09.400
significantly better faster more powerful that's why i like it but the actual results that you're
00:39:16.000
going to see are going to be basically a saint the same across the board so the good news is if you
00:39:23.800
have a preference one or the other you really you know you swear by sky scanner you love kayak go for
00:39:30.200
it it's not it's not going to make a huge difference in the actual fares that you see but what i would say
00:39:36.140
is that you might want to differentiate between where you search for your flights and where you book your
00:39:42.740
flights because the price tends to stay the same i like to search for my flights on any one of those
00:39:48.620
kind of meta search sites where i'm comparing across airlines to making sure i'm getting the best price but
00:39:54.180
then when i actually go to book i typically like to book directly with the airline and that's for two reasons
00:39:59.820
one because there are certain federal protections that you have when you book directly with the airline
00:40:05.560
for instance there's something called the 24 hour rule this is a federal law that says when you book a
00:40:11.860
flight directly with an airline you from the moment you hit purchase you get a 24 hour grace period
00:40:18.080
during which you can cancel your purchase and get a full cash refund no questions asked that is not
00:40:24.800
the case under federal law when you book through an online travel agency they might have their own
00:40:30.240
policies or or offerings on those many of them do but they don't because they don't have the weight of
00:40:36.420
law behind them they're just not quite as attractive in my mind but second when you book a flight directly
00:40:42.980
with an airline if something goes wrong with your itinerary if the flight schedule gets changed if there's
00:40:50.360
thunderstorms if you decide to cancel or this or that it's much easier to handle or change your itinerary
00:40:57.600
if you can just deal directly with the airline rather than having to deal with a middleman because not only
00:41:03.360
you know is a middleman going to be a more just an arduous process but then you've got not only the airline's
00:41:09.700
policies but the middleman's policies to deal with as well and so this for simplicity's sake it ends up being
00:41:16.260
far far preferable if anything needs to change with your itinerary if you've booked directly with the
00:41:21.620
airline so differentiating between where you search and where you book all right so book with the
00:41:26.160
airlines and you talk about you can take advantage of that 24 hour rule when you book with an airline
00:41:30.420
to kind of it's a way to find better prices it's kind of arbitrage right that's right so i mean you
00:41:36.320
know i'll give you one example there was a gentleman that i interviewed for the trip who had really
00:41:43.040
wanted to travel to japan he was very very excited to be able to visit and when some cheap flights
00:41:50.940
popped up for him he was like really excited to book them i believe they were initially i'm trying
00:41:57.200
to find the exact price initially 572 dollars he booked them but then within 24 hours all of a sudden
00:42:05.020
a better flight popped up he was in dc from richmond to tokyo for even cheaper so he said well look
00:42:11.780
richmond's not that hard to get to i'll save the save you know 100 i'll go down to richmond and get
00:42:16.740
a cheaper flight and because this new fare popped up within 24 hours he could cancel the old itinerary
00:42:22.800
and book the new ticket from richmond to tokyo well then lo and behold again within 24 hours of doing
00:42:28.500
that another cheaper flight popped up this time out of dc to tokyo for just 584 bucks round trip even
00:42:36.400
better than the initial richmond flight so he canceled that one booked the new dc tokyo flight
00:42:42.520
for 584 and ended up being able to take a great trip a much more convenient trip than what he had
00:42:48.060
initially booked and so the key to remember is that the 24 hour rule can help you in a few different
00:42:55.860
ways it can help you if you're not a hundred percent sure you want to take a trip but you see a really
00:43:00.780
good fare so if you book it what that does is essentially just freeze the price for 24 hours
00:43:07.200
and give you time to decide do you want to keep this trip or would you rather just cancel and get
00:43:12.380
your money back maybe you need to consult with a significant other travel partner but they're in a
00:43:17.280
meeting rather than risking the fare disappearing which which does happen especially with really cheap
00:43:23.620
fares you could book it lock it in for 24 hours and then cancel later if you decide you don't want it
00:43:30.160
but then it also the 24 hour rule lets you take advantage like with this gentleman donald and his
00:43:35.920
flights to tokyo where if the price drops after you book which happens more often than you would think
00:43:42.540
airlines do have what are called fare wars where they're essentially just ratcheting down the price
00:43:47.580
to compete with one another if there's a fare war going on you can book your flight but then if the
00:43:53.600
price gets cheaper or if it switches from a connecting flight to a non-stop flight you can cancel your
00:43:59.740
itinerary book the new one and take advantage without having to pay anything extra and in fact be able to
00:44:05.760
save the difference and you you also will highlight that you can do this with southwest airlines use them
00:44:10.440
as an arbitrage tool so typically southwest we think of like it's a budget airline right but oftentimes you
00:44:15.960
can find better deal with the other airlines so you're saying use southwest airlines to get to your
00:44:20.280
initial destinations you can lock in that kind of you know basically affordable price but then you know keep
00:44:25.440
looking for better deals with another airline yeah like okay so i've got a i've got a wedding that i
00:44:30.800
need to go to this september and as soon as i got the the dates for that wedding what i did was went
00:44:37.720
ahead on southwest.com and i just booked the best flight i could find you know with a reasonable price
00:44:43.280
to the destination for those wedding dates and the reason why i booked it on southwest and especially i did
00:44:49.660
so with southwest points that i had is that southwest flights are free to cancel if you book with points
00:44:56.700
you just get all those points redeposited with no fee or anything if you book with cash they just hold
00:45:03.180
your funds as a you know the exact amount as travel credit for a future trip and so what that does is
00:45:10.160
essentially lets you set a price ceiling so in this instance i believe it paid like 350 for the flight
00:45:17.520
and what that said was i said 350 as the maximum so if the price went down on southwest well i'll just
00:45:24.780
cancel and i'll rebook it for the 300 price if it does go down if it goes up to 400 450 no worries i
00:45:33.200
already got my 350 ticket if it goes down on another airline let's say american offers that that flight for
00:45:40.300
the on those dates for 250 well great i'll book that american flight i'll cancel my southwest one for 350
00:45:46.680
and end up being able to take a cheaper trip so either way what it ends up allowing you to do the
00:45:53.880
southwest arbitrage is essentially create a heads you win tails the airlines lose situation and lord knows
00:46:02.100
we need more of those because it feels like it's more often the other case you know the that the
00:46:06.220
airlines are usually the one to try to get one over on you and so finding instances like this where
00:46:11.380
you can say this is the most that i'm going to pay and if there are any price drops between now and
00:46:16.160
then which there often are considering how volatile airfare is uh you can take advantage and end up
00:46:22.480
saving the difference another advanced tip you highlight that can save you a lot of money especially
00:46:27.460
if you're flying internationally you mentioned this earlier let's say you want to go someplace in
00:46:31.100
europe like brussels but like direct flights from brussels from your you know from chicago are crazy but
00:46:37.240
if you find a place to london that's super cheap basically you said you can just build in a layover in
00:46:42.360
london and then as soon as you're in europe it's pretty cheap to fly anywhere in europe after that
00:46:46.320
point yeah that's exactly right you know so i call this the greek island strategy the idea that if you
00:46:52.660
were to search for a flight from new york to santorini oftentimes they're closer to like fifteen
00:46:58.020
hundred dollars especially if you're traveling in the summer but flights from new york to athens are
00:47:03.200
regularly 450 bucks and oftentimes non-stop whereas there are no non-stops to santorini from
00:47:10.360
the u.s once you get to athens it's really easy to hop a budget flight hop a ferry something else to
00:47:17.120
get to the to the islands for you know 50 bucks 75 bucks and so not only do you end up save you know
00:47:24.440
being able to pocket uh get a 66 percent price reduction off those fifteen hundred dollars santorini
00:47:31.440
flights but you also again can build in that free layover where you can take as much time as you'd like
00:47:36.980
in athens before continuing on to santorini and make it a free layover free two-in-one trip
00:47:43.940
looking for especially when you are traveling whether it's somewhere remote or somewhere even
00:47:50.600
just where there's a the destination there aren't many cheap flights popping up getting you know we
00:47:55.460
talked about getting creative when you might not have full flexibility keeping an eye on cheap
00:47:59.560
nearby airports knowing that once you get to europe once you get to southeast asia it's really easy to
00:48:07.840
then continue on from the hub where you arrive to your final destination on another flight and the
00:48:14.880
reason why you need to take a little creativity and search this yourself is that the airlines themselves
00:48:21.080
aren't going to sell tickets on rival airlines and so maybe the cheapest flight across the ocean
00:48:27.620
let's just say it's on british airways but then the cheapest flight from london down to brussels
00:48:34.640
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
00:48:42.620
able to buy that as a single itinerary with british airways and klm because they're rivals they don't
00:48:48.640
sell one another's tickets and you're not going to see how cheap but instead by buying one flight to
00:48:54.480
london and a separate flight from london to amsterdam you are able to build yourself the
00:49:01.100
cheapest itinerary and so that's why it's important especially when you have these long
00:49:06.040
haul flights over an ocean to see if you can do it cheaper by flying into a different gateway
00:49:11.180
and then continuing on with a different airline to your final destination
00:49:15.220
another tip to find cheap flights is mistake fairs i guess you're kind of you're kind of
00:49:20.440
hinting that you think that great deal you got to milan was a mistake fair what are those and like
00:49:25.300
why do they happen and how do you find them oh yeah absolutely it was there was no question that
00:49:30.240
was a mistake fair mistake fairs are interesting because they pop up more often than people would
00:49:35.660
realize and they they end up getting honored much more often than people would think you know
00:49:41.680
obviously that 130 flight got honored but that's not the only mistake fair i've gotten in my life
00:49:46.200
i've gotten a flight from the u.s to japan for 169 round trip like half of my co-workers it's got
00:49:53.740
two flights got a business class round trip flight to southeast asia for 550 round trip a ticket that
00:50:01.220
normally costs five thousand dollars to you know bangkok or bali or vietnam and those types of deals
00:50:07.400
pop up quite regularly right really you know eight ten twelve times a year usually like i'm looking
00:50:14.800
at one in just a couple months ago there were mistake fair to iceland where it was boston to
00:50:20.400
reikovic for a hundred dollars round trip dc to reikovic for 129 denver to reikovic for 149 round trip
00:50:28.080
those types of deals do pop up regularly they pop up for a number of reasons so the classic case was
00:50:34.780
like with that milan deal where maybe they just accidentally forgot a zero at the end and sold
00:50:40.060
it to me for 130 rather than 1300 there are other reasons why maybe the again airfares set algorithmically
00:50:48.020
nowadays and so it's much more difficult to often figure out what you know it will one change here
00:50:54.260
produce a sort of anomaly in the end result of some other fares and so they do pop up still pretty
00:51:01.720
regularly the key when a mistake fair pops up is to book it as quickly as possible again taking
00:51:07.980
advantage of the 24 hour rule because you know as soon as they're fixed they're gone i remember
00:51:13.320
looking at a flight once from the u.s to india i believe it was from dallas to india for 212 round
00:51:19.340
trip and i was so excited you know i was messaging friends hey who wants to take this trip by the time
00:51:25.060
we sort of found i recruited a friend to go travel we planned our itinerary and everything we we took
00:51:30.920
two hours to plan where we were going to go and when before then booking our flight and i kid you not
00:51:36.740
30 seconds before i went to book the flight it disappeared the 212 mistake was fixed and so by
00:51:44.240
by dawdling by by taking our time we ended up missing the deal uh so we mentioned that prices right now
00:51:51.500
are just crazy for summer summer travel i guess your take is if you really want to travel that place
00:51:55.960
it's better to hold off you want a cheaper flight absolutely look if you have the opportunity to
00:52:01.220
travel in the fall or beyond really labor day and beyond fares are likely to be 50 percent lower or
00:52:07.480
more i mean you just you see tons of it i think people have made the mistake of assuming that cheap
00:52:14.040
flights are gone forever when in reality they're just gone for this summer we are still living in what i
00:52:19.260
call the golden age of cheap flights it's just it's at this point as it would be in any at this in june
00:52:26.000
of any summer it's virtually impossible to find cheap summer flights yeah i think i read somewhere
00:52:31.540
that flights are up by a third the summer is that right yeah they are significantly rebounded from where
00:52:38.920
it was a year ago still cheaper when you look up compared to where it was a decade ago but you know
00:52:44.220
small comfort for folks who are kind of got used to those really cheap pandemic era flights and then
00:52:50.040
are getting a bit of sticker shock this summer okay so flights are really expensive in the summer
00:52:54.360
any year but they're especially high this year because of pent-up travel demand during the pandemic
00:53:00.220
the airlines laid off pilots and they didn't hire as many people and now everyone wants to travel
00:53:04.960
but even if those things get smooth out will prices go down in the fall like they usually do
00:53:10.740
like will will they go back to the normal fall levels that we're used to or things like inflation
00:53:16.820
or an oil price is going to keep them from going back to the prices that we're normally accustomed to
00:53:22.580
uh they will go back and you don't have to take my word for it you can just go look at the prices for
00:53:28.940
the fall right now you know i i took a look before chatting with you and and you know just a couple
00:53:35.340
sample fares for instance if you wanted to fly right now from chicago to cancun july
00:53:40.720
21st through 29th 583 september 21st through 29th 233 you know austin down to a ruba july 8th through
00:53:49.400
15th 951 round trip november 8th through 15th 293 round trip if your schedule allows you to travel
00:53:56.540
in the fall or the winter you really can take advantage of a lot of the cheap flights that are
00:54:01.320
still available but you want to try to book those sooner rather than later if you wait again to the
00:54:05.800
last minute to book those if you wait till september to book your flights in october it could be
00:54:10.540
kind of difficult to get something cheap whereas if you try to get those on the books now and give
00:54:15.620
your today self something to look forward to it's going to end up being better both for your
00:54:20.360
happiness and for your wallet so you guys big takeaway there if you're going to plan a trip
00:54:25.420
plan for the fall and even if prices do go up a little bit there's still good deals to be found
00:54:30.580
absolutely absolutely look it's if your schedule allows it try to avoid frankly flying in the middle
00:54:38.240
of summer that's when fares are going to be most expensive if cheap flights are important to you
00:54:42.640
traveling in the middle of summer is generally not going to be the best time to do that but even if
00:54:47.920
you really want to travel in summer and you really want to still get a good deal having to plan well
00:54:53.600
ahead but what i like to say is if you want to travel peak season always book opposite season you
00:54:59.520
know in the same way that swimsuits are going to be cheapest to buy in the winter same with your summer
00:55:04.760
flights purchasing those in the winter and so what that means is right now in the summer the cheapest
00:55:10.200
thing to buy on in stores are those winter coats the cheapest flights to buy right now are those
00:55:15.840
winter holiday flights so think about booking your christmas new year's flights now while they're going
00:55:20.820
to be much cheaper than if you wait four or five months and are trying to book them at the same time
00:55:25.440
as everybody else and seeing really expensive fares at that point well scott this has been a great
00:55:30.060
conversation where can people go to learn more about the book in your work
00:55:32.740
absolutely so the book is available at any bookstore they some of the large conglomerate
00:55:39.060
selling books online or your local independent bookstore it's called take more vacations
00:55:43.540
and you can sign up for alerts about cheap flights popping up from your home airport at scottscheapflights.com
00:55:51.240
no apostries no underscores that's scottscheapflights.com
00:55:55.440
fantastic well scott kyes thanks for your time it's been a pleasure
00:55:57.440
my pleasure brett thank you so much for having me
00:55:59.820
my guest there is scott kyes he is the founder of scottscheapflights you can check that out at
00:56:04.920
scottscheapflights.com also check out his book take more vacations available on amazon.com and
00:56:10.000
bookstores everywhere also check out our show notes at awm.is slash cheap flights where you can find
00:56:13.940
links to resources where we delve deeper into this topic
00:56:16.020
well that wraps up another edition of the awm podcast make sure to check out our website at
00:56:27.120
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00:56:30.620
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