Are you ready to get started with points, miles, and all things cheap travel? It all starts with airfare, so in this first installment of our new Starter Kit series, Gunnar and Kyle walk through how to find the cheapest flight possible, every single time. The guys cover the tips, tricks, tools, and (most importantly) the mindset you need to find cheap flights and start traveling more for less.
Are you ready to get started with points, miles, and all things cheap travel? It all starts with airfare, so in this first installment of our new Starter Kit series, Gunnar and Kyle walk through how to find the cheapest flight possible, every single time. The guys cover the tips, tricks, tools, and (most importantly) the mindset you need to find cheap flights and start traveling more for less.
Our Starter Kit is sponsored by Thrifty Traveler Premium, the world’s best flight deal service. Get $20 off your first year of Thrifty Traveler Premium flight deal alerts - use promo code “START” at thriftytraveler.com/premium.
00:00 - Kicking off our Starter Kit: How we got started
2:52 - The two most important rules for finding cheap flights
7:09 - Why you NEED to start your search with Google Flights
11:24 - One-way flights versus roundtrip bookings
15:34 - Learning how to follow the deal, not the destination
16:51 - Positioning flights: the key to cheaper international fares
18:56 - And the risks of using those positioning flights…
20:35 - The intricacies of airfare & what to avoid
24:38 - The art of rebooking flights to save even more
30:26 - Busting bogus airfare myths
33:35 - Your Flight Plan - Recap & to-dos from Ep. 1
36:48 - Up next in Starter Kit…
Vol. 1 Flight Plan:
Think “Flights First”: Plan your trips around the best flight deals and book them before anything else
Book quickly: Utilize the 24-hour flight cancellation rule to get the best deals. Book fast, figure out the details later.
Get to know Google Flights: By far the most powerful flight booking tool and the key to saving on airfare. Use its price calendar, the filters, and price alerts to book when prices drop
Start re-booking your flights: Set up price alerts on your existing flights and rebook when prices drop. It’s the most underrated way to save big on travel.
Related episodes:
https://thriftytraveler.com/podcasts/ep-72-google-flights/
https://thriftytraveler.com/podcasts/episode-47-post-booking-checklist/
https://thriftytraveler.com/podcasts/episode-25-book-the-cheapest-flight-every-time/
https://thriftytraveler.com/podcasts/episode-50-inside-thrifty-traveler/
https://thriftytraveler.com/podcasts/ep-70-top-10-flight-deals/
Produced and edited by Sylvia Thomas
Video editing by Kyle Thomas
Show music: “All That” by Benjamin Tissot
Yo, welcome to the show. I'm Gunnar Olson, a reporter for Thrifty Traveler and a flight deal analyst for Thrifty Traveler Premium. And joining me for this special series in every episode of the Thrifty Traveler podcast, it's Thrifty Traveler executive editor and our Points and Miles Sherpa, it's Kyle Potter.
Kyle, welcome to Starter Kit.
We're really sticking to the Sherpa thing, huh?
I like Sherpa, yeah. All right. You're, you're our guide through the mountains, through the wilderness that is Points and Miles. This is our first edition of Starter Kit, and today we're talking about the fundamentals of finding and booking the cheapest flight possible.
We're gonna go over two fundamental rules to live by, give you an overview of the most powerful flight booking tool there is, and do some airfare myth-busting too at the end. So Kyle, you and I are, are both now what we would consider Points and Miles sickos, a term of endearment for both of us, but it wasn't always that way for either of us.
How and why did you get started in travel rewards?
Well, you know, I think back, uh, about a decade ago when my wife and I were planning a trip through Southeast Asia and Japan. We went to Thailand, Vietnam, and then Japan. And that did two things for me which I think are just so critical for sending you down the rabbit hole of learning and caring about this stuff.
First and most importantly, it was just an amazing trip. Incredible, life-changingly cool experiences, and I think that's really important. But two, in the process of planning that trip and trying to piece things together and find the cheapest fares and use what little at that time Points and Miles that we had saved up, I started to see the travel booking process as a puzzle, and really enjoy something that to many people, hopefully not many people that are listening to this, view as extremely frustrating.
And that that part of it made it really rewarding, and I really think that you need both sides of that coin in order to really start to care about this and make it a piece of your life.
I think that's such a relatable story in Points and Miles. That's exactly the way that people get into it, is they realize that the puzzle is kind of fun and the whole journey of it is part of the point.
Um, for me, I got into Points and Miles because I needed to save on flights to go skiing, which is already a hobby that I couldn't afford. So I really couldn't afford to go buy plane tickets to go out to the mountains and go skiing every year. So actually, I turned to Thrifty Traveler, but way before I joined the team, and, uh, I was watching and listening to you guys all the time, giving me tips on how to get better at this.
And, and look at us now, Kyle, hosting Starter Kit to help others get involved.
Who, who would've thunk it? Who'd have thunk we'd be here?
Okay, today on the first episode of Starter Kit, we're going over all the best strategies to find and book cheap flights. We're gonna talk about the two most important rules for buying airfare, how and why all your trips should start with Google Flights, how to identify the right fare, and how to get the best deal on flights.
All that and more. Welcome to Starter Kit from the Thrifty Traveler podcast.
Okay, we're back. Let's jump into our discussion for how to find and book cheap flights. And I think we have to start with two rules that are core principles to airfare, one that is a literal law and another that we came up with. And I think we're gonna start with our rule. Kyle, what is the flight first rule?
It's more important than federal law, apparently because we're starting with it first. Uh, that sounds like a joke, but I actually think it's true. I think this is the single most important change that you can make in your travel planning process to find and book cheap flights. And it is exactly what it sounds like.
So most people, as they plan a trip, they request time off work, they maybe even book a hotel or their cruise or whatever they're gonna do, and only then they go back to look at flights. And then you're locked in. You have to be somewhere on September 17th. You have to come home on September 24th because that's when you check out of your hotel, and you are now at the whim of whatever the airlines want to charge you.
And maybe you get really lucky, but you probably don't, and you probably see some atrocious airfare, and you just have to swallow it. So instead, you flip that entire travel planning process on its head, and you look at flights first. You follow the flight first rule before you request time off work, before you book your hotels, before you do all of those things because that gives you the flexibility to get on the plane when it's cheapest.
And then from there, you build out the other parts of your trip. You request that time off from your boss. But by starting that way, it gives you the most wiggle room to save on flights because changes by even just a day or two can save you hundreds of dollars on domestic airfare. If you're talking about a big trip abroad, you could easily save thousands for a family of four or more.
Yeah. This is really smart. Airfare is the most volatility priced part of your trip almost no matter what. So booking your flight first or, is gonna help you save. Let's get to the letter of the law. Uh, this has to be my favorite law in the world, Kyle. What is the 24-hour rule?
The 24-hour rule is a federal requirement that whether it's a US airline like American or Delta or United or a foreign carrier like Lufthansa or Swiss or EVA Air, if a flight touches US soil, an airline is required to issue a refund when requesting a cancellation within 24 hours of booking.
This is non-negotiable. They cannot stick you with, like, just a travel credit or a voucher. You can get your money back if you have buyer's remorse or you s- book that flight and you start to scope out your plans and it turns out, oh, you know what? This isn't gonna work, or you booked your flight and the hotels are just crazy expensive, and you can't stomach it.
You cancel for a full refund, get that money back. I think really importantly, some big exceptions to this, namely many airlines don't allow you to do this booking last minute. So you can't book a flight today for a trip tomorrow and then say, "Oh, well, you know what? I can't do this." Uh, the federal government only requires airlines to honor this rule when booking at least seven days before departure.
Some airlines do this a lot better. Delta, for example, allows you to book whenever and cancel as long as you cancel within 24 hours. Others take that full seven days.
Yeah. It's an amazing rule. It, uh, has definitely helped me, you know, get my PTO approved by you, my boss. And to, uh, get a text back from my wife to make sure that we can actually make this work.
Now I just go ahead and book the flight that I want when prices are the cheapest, and I can have, I have 24 hours to figure it out, get that text back, or, uh, have you deny my vacation request.
I really love those emails from you saying, uh, "I'm gonna leave for three weeks. You need to respond by the end of the day."
Um, is that how people should use the 24-hour rule?
I think so. Yeah. Uh, you know, I think the, the perfect examples are this situation where you see a great deal, you wanna book it, you're not sure if it's gonna work with work and all of the other logistics that you need to figure out. Maybe most importantly, it's amazing for mistake fares, which is the epitome of, you know, a, a flight that should probably cost $1,500 and for some reason it costs $201.
You don't know if you're gonna be able to take that trip. You don't have the time to figure that out because mistake fares can disappear like that. So you book it now, you ask those questions later knowing that you've got this 24-hour window to sort things out, and if it doesn't work, you cancel that for a full refund.
Awesome. Okay, let's move on and talk about Google Flights 'cause I think this is the most important travel tool, period. Every trip of mine starts and ends with Google Flights flight search, but it goes a lot further than that. Uh, let's highlight a few of the tools in Google Flights that we find most useful.
And Kyle, you start. What's your favorite feature of Google Flights?
I mean, if you wanna hear me talk about this for, like, 15 minutes, go back and listen to our Google Flights episode from earlier in the summer of 2026. But it's the calendar, and it's because it is what supercharges the flight first rule So with Google Flights, you, you start searching for your trip.
You search that September 17th to the 24th, uh, trip for wherever you're trying to go. And then there is a two-month calendar that you can pull up where it will show the dates in green where it's cheapest to actually fly. So if in fact it's, you know, significantly cheaper to fly, to leave on September 15th instead of the 17th, you're gonna see that very clearly.
And then Google Flights takes it to the next level where if you've already selected those dates and you're not in the calendar anymore, but it's $200, $500 cheaper to depart one or two days earlier, it'll give you a pop-up notification and, uh, and tell you, "Hey, by shifting this trip by a day, you're gonna save $200, $300," whatever the case is.
It is just so enormously powerful and user-friendly to an extent that no other site even comes close.
Yeah, it's kinda shocking to see the variability in flight pricing day to day when you do pull up that calendar. That's why it is such an important tool. I will give a shout-out just to the filters of Google Flights.
When you're searching for a flight, you get the search results and you'll see a toolbar on the top that has a ton of filters. You can filter for ha- having a carry-on bag or a checked bag even. You can filter for the length of your layover. You can filter for what airports you do or don't want to have a layover at, the time of day for your flights, what airlines you wanna fly, how many stops you're willing to stomach.
Uh, the filters go on and on. And the best part about the filters is that once you put those in, the filters will inform the calendar. So when you pull up the calendar again, it'll show you the exact, uh, fares that match all the filters that you've put in, and that also goes for the Explore tool, which I assume we'll talk about here next.
Oh, it's, this is maybe the single most powerful tool on the entire internet for finding a cheap flight, and it is perfect if you just need a cheap getaway. You don't care where you go. You'll go anywhere you can find a cheap flight. This is Google Flights Explore to a T, because you put in your home airport.
You can either put in your travel dates or just say, "I wanna take a weekend trip in October," or, "I wanna take a two-week trip in April." And then you literally spin around the globe and explore and see prices on the map of just, of the cheapest flights that you can book that fit your parameters. This is also amazing if you say, "I wanna get to Europe, and you know, I'd love to go to Paris or Madrid, but I'd be willing to train between them or I'd be willing to book a cheap Ryanair flight between them.
I just wanna get the cheapest fare I can get to actually cross the pond." Google Flights Explore is gonna allow you to do that. You can search at Google Flights. You can just enter instead of Paris and Madrid and wherever else, just enter Europe- And then it's gonna pull up that Explore map and it's gonna show you again in green exactly the cheapest destination for your trip that's gonna get you there at the lowest price.
Yeah. Clear your schedule and spend a few hours with Google Flights Explore. It is kind of addicting too. It's a very, very fun tool.
We just clear- just have a great little afternoon or evening with Google Flights Explore. That's just normal things.
Yeah. All right. Um, one more I wanna highlight. Uh, I am the self-declared prince of Google Flights price alerts- Yes, you are
Kyle. Um, you can monitor the prices of the flights that you're hoping to book or have already booked up to 100 times, which I have maxed out several times in my life using Google Flights. Uh, but Google Flights price alerts will do just that. They'll send you as lo- so long as you have a Gmail account, it'll send you an email if the price of your flight goes down or up.
So you can constantly track the price of things. I use it, of course, when I'm looking to book a flight, and also definitely when I've already booked a flight. We'll get into that a little more later. Um-
Can I... I think our next prop for the office needs to be a crown for you- ... that says Google Flights Price Alert Prince.
I will take that. I'll take that crown. Kyle, I want you to highlight one more feature of Google Flights, and, uh, it answers a question we got from Thrifty Traveler Premium member Catherine. She asks, "If you find a good deal for one-ways but can't find a return, how far out is that okay, and at what point do you need to be worried?
I've been too nervous to pull the trigger on some because I can find one-ways that work but not another. I'm also a teacher, so flexibility has its limitations during the school year." How, how should Catherine go about getting the context for what is a good deal and when she should book?
Well, first I think an important teaching moment here is that, A, Google Flights and most airlines allow you to book 330 days out, 11 months out.
So if you're looking right now as you're listening to this in late August, you can look out as far as late July Two is that one-ways, while give, it gives you more flexibility often, and especially for international trips, but increasingly domestic as well, booking one-way separately tends to cost you significantly more than double the round-trip price.
So I would maybe steer clear of that and just give yourself a little bit more time until you can actually book that round trip. All of that said, Google Flights has this amazing price history chart for basically every fare that you look at. Sometimes it won't show up. I think it depends on how many people have searched for that route and have price alerts set for it, too.
But it will show you how the price has changed over time, which can be a really good key to tell you, is this a good deal or is it not? It'll also kinda show you on a sliding scale what Google determines to be a good deal for this particular flight that you're looking at, which is just another bit of evidence that can give you some comfort of whether this is a good fare or not.
Sometimes it'll even give you predictive analyses, like saying something like, uh, "We expect the price of this fare to jump $100 in the next 10 days," or something like that. Which I, you know, don't take it as gospel, but it is a good, it's good context. If you have no idea what a flight between, you know, Boston and Zurich is supposed to cost, unlike us who have weird encyclopedic knowledge of this, you could always just use those kinda Google Flights, uh, predictions as some context there.
It's really, really helpful. All right, Kyle. Um, if anybody out there has listened to our show before, you know that maybe the most dangerous drinking game on Earth is the drinking game where you drink every time we talk about flexibility. Uh, when are some times that when it pays to be flexible when booking flights, Kyle?
I mean, it's a good thing we don't... Well, actually, we do have booze in this office. It's a good thing we haven't brought it onto the table because we would be wasted every time we record one of these. I mean, I, you can't say enough about flexibility. There's a reason why we harp on this ad nauseam is because if there is one single silver bullet- To travel more for less, it's not points and miles, it's not even Google Flights as much as we love both of those things.
It is flexibility. If you can't be flexible at all, odds are you're not gonna be able to travel more for less. Now, that doesn't mean you need to be able to get up at the l- last minute and go on a big trip. It's not that. It's just having the flexibility to travel on a different d- day than the initial September 17th to 24th timeframe that you decided on, or, you know, travel in the spring or the fall instead of the peak summer when fares are typically at their highest.
Yeah, I think, uh, crucially, like, uh, what you're saying here, especially if, say you're a teacher out there and you wanna book the cheapest flight possible, and you're saying, "Great, all the cheapest flights are in October." What we're saying is you don't necessarily need to change everything that you do about travel.
Flexibility can be as simple as changing, you know, one day. It could be as simple as changing an hour or two. Book that first flight of the day or the last flight at night. That's always gonna be cheaper than kinda those middle of the day flights. Um, these small adjustments can lead to big savings. You also can be flexible on, for instance, what airline you wanna fly.
Uh, if you're willing to take a connection instead of booking the expensive nonstop out of your home airport, you could save big money doing that, too. Uh, loyalty to airlines typically costs you money, so being able to branch out and pick an airline based on the price is also another way that flexibility is important.
Um, can you tell me about being flexible with your departure and destination airports? I think this is something that people overlook.
I, I think this is maybe the biggest one, and the, the, you can take this to an extreme which, you know, what we, what we tell people is follow the deal, not the destination.
If you're willing to go wherever a cheap flight will take you, like for example, when I woke up one morning to a Thrifty Traveler premium alert that I could fly from Minneapolis to Bogotá for $221 round trip for my wife and I instead of the $900 or more that it typically is. It's like, you know what?
Bogotá wasn't that high on my list, but it's high enough that $220 is well, well worth it. But again, you know, going back to the example we gave before, if, if you're flexible about how you get to Europe And you're flexible to get where you eventually want to go by train or by plane. That too is going to save you.
There are so many different variations of what flexibility looks like. And to the point you made, it isn't cut and dry. It isn't just you need to travel in the fall. That's great if you can, but if you can't, traveling on a, you know, getting on the plane on a Tuesday or a Wednesday instead of a Sunday or a Monday is almost always gonna save you at least a couple of bucks, if not hundreds, and in some cases, a thousand or more per ticket.
Yeah, for sure. Okay, um, we have another question from a Thrifty Traveler Premium member, Neil, that I think is related to this. Neil asks, "Can you go over how to position to different airports to get the best deal? One way I found was to look at flight connections, but is there a better way? For example, I'm in Cleveland.
Do I go east or west? So do I go to JFK or Chicago or even LAX for the best deal on flights?" Uh, what's Neil talking about here?
Positioning flights are really critical, especially for people who don't live on the, in the big hubs on each coast. Um, it is a way to piece together your trip where you basically build your own connection.
So instead of starting from your home airport, starting your search for, for us here in Minneapolis or for somebody who lives, you know, in Fargo, North Dakota, starting from there. You search from one of those bigger hubs, and preferably one of those bigger hubs that you can easily get to for cheap. So, you know, for many people, you can hop on a nonstop flight to somewhere in the New York area for a relative bargain.
Same goes, in many cases, for Boston, to a lesser extent, Chicago. Um, you know, if you're in the middle of the country, certainly LA or San Francisco or Seattle. So I would start by thinking about the airports that you can get to cheaply, and then ask yourself, "What airports are most likely to have the cheapest fares to get to my final destination?"
If that's in Asia or Australia, we're talking West Coast. So Seattle, San Francisco, LA would be the big ones. If you're talking Europe and other parts of the world, up and down the East Coast, New York, Boston, DC, Miami, sometimes Atlanta, uh, in many cases Chicago, I would loop into that as well. And so then you do, you book your flight separately.
You book a positioning flight to get to that bigger hub. You give yourself a really long buffer for that connection. I'm talking four to five hours in some cases. And then you separately book that international flight and, but in doing so, you can often save a ton compared to what it would cost just searching from Minneapolis to London or Minneapolis to Tokyo.
Yeah. So there is a little bit of risk here, which I wanna drill down on, and Mark asked us a question. Another premium member, Mark, said, uh, "Another question regarding positioning flights. What are the guidelines for when to fly in the day before and book an overnight hotel maybe as opposed to rolling the dice and flying in the same day with a certain number of hours for a layover?
When flights are not on the same itinerary, I'm afraid that I'm setting myself up for problems if I don't build in sufficient layover time." What do you think about Mark's concerns here?
I mean, Mark and everybody is wise to be wary of this because the problem is, is that when you have this kind of, these flights booked separately, they're not on the same ticket, it's an unprotected connection.
Which means if your flight flying into New York City is delayed by four or five hours and you miss that flight from New York City to Paris Game over in most cases. That airline that was supposed to fly you over to Paris has no responsibility to put you on the next flight. You just missed your flight.
So more time is always better. You know, my rule of thumb is typically somewhere in the neighborhood of four to five hours for those bigger connections. If it's the summer in the East Coast when storms are notorious for wrecking flights, I would give it even more time. If it's a really, really important trip, like you're boarding a multi-thousand dollar cruise or, you know, it's a multi-generational family trip, once in a lifetime kind of thing, flying in a day earlier, booking, you know, a cheap hotel near the airport just to make sure that you can get there and have plenty of time to board that big trip abroad the next day is not the worst idea.
Yeah. That's really smart guidance. Positioning flights are, uh, a, a next level travel booking technique. We highly recommend it. Um, let's talk about fares. When it comes to buying airfare, I think it's important to remember that not all fares are created equal. So let's start here, Kyle. What is basic economy, uh, that lowest fare, and what should people know about it?
Avoid at all costs unless if you know what you're getting into. So let's start with what you're getting into. Basic economy was the major, uh, US airline industry and increasingly foreign airlines' answer to budget carriers. It is how they compete, competed on price with the likes of Spirit and Frontier, which means you get a lot less.
I think most importantly, you can't pick your seats for free. In many cases, you're just gonna be randomly assigned a seat, so if you're traveling as a family, that can be, you know, a real killer. Uh, you, in some cases, can't even bring a carry-on with United Airlines at least flying domestically. Maybe most importantly, you cannot change or cancel your flight without hi- getting hit with some pretty significant fees.
If it's, if you're booking a basic economy ticket flying abroad and you're tr- you need to cancel that flight, you're gonna get hit with $199 fee, which means if you booked for, you know, $500, almost half the cost of your ticket is gone if your plans change. So if you need some flexibility to change or pivot, if you're not sure about the trip, if you are okay with the deal, but you think it can get better, you just gotta suck it up and pay more for the main cabin economy fare.
Yeah. With all of the US airlines, at least the major ones, Google Flights lays all of this out for you before you ever even get to the airline website. So you don't have to feel like you're getting tricked. It's all laid out. You can see exactly what you're gonna get with each fare. But those main cabin fares are gonna be a lot more inclusive.
They're gonna include seat assignment. They're even gonna include a checked bag on long-haul flights overseas in most cases. Um, and they're gonna in- include the ability to change or cancel for at least a voucher, so you have an airline voucher that you can use going forward. Um, can we also talk about where to buy your fare?
Because I think that matters a lot to us. Uh, our recommendation to travelers is always to try and book directly with the airline when you can instead of through an online travel agency, what we call OTAs, websites like Expedia or Kayak or Travelocity. Why do we recommend booking directly with the airline?
Because things go wrong in air travel. Uh, it is unavoidable. There are going to be delays. The more you travel, the more you're gonna get delayed. Uh, ultimately, you might have a flight or two canceled, and when things go wrong in air travel, having a flight that you book directly with the airline cuts out the middleman.
Because if that happens, and you booked through somewhere like Expedia, you gotta talk to Expedia, which then has to talk to Delta or United or American to get you rebooked or to get you your refund or whatever needs to happen in order to unwind what has gone wrong. And that adds a layer of complication that I would say 9 times out of 10 is just not worth whatever you might be saving.
I think in many cases, people ha- just have an impulse to go to somewhere like Expedia or Skyscanner or Hopper because they believe that that's gonna get them the best deal. I would say increasingly, the fares that you can get directly booking through Delta or Southwest or United or wherever are on par with what you can get through these third-party sites.
So there's increasingly just not an upside to booking through these third-party platforms. If there is Is it worth $15 in order to have this middleman in your reservation that's gonna complicate things if things go wrong? I mean, that's a personal question. To me, absolutely not. The number that I would need to justify that is probably somewhere in the neighborhood of $100 to $200 or more round trip.
Yeah. My brain's ability to go to worst-case scenario when I'm thinking of all the things that could possibly happen to my travel day, I, I, I, I will not allow myself to entertain booking with an OTA unless the savings are incredible. You know, unless it's like, "I can't avoid ... I, I cannot miss this deal because it's so good."
So booking directly is always my strategy.
You are just a ray of shun- ... sunshine today.
All right. Um, let's talk about what I think, uh, i- is the next level to booking cheap flights, and it's when you graduate from just booking travel to rebooking travel. This is one of my, I'd say, my calling cards, and maybe you would say is one of the most annoying things that you have to hear about every day.
No, I love it.
Okay. Uh, it's my philosophy you're never done booking a trip until you're back at the baggage claim at your home airport after the trip is done. I, I really think that tinkering with your trip can save you a ton of money when prices drop. Uh, it can also make your trip easier or more convenient if that route that you initially wanted to book that was too expensive becomes available.
Uh, and it can also make your trip more comfortable, uh, if you're booking maybe with points and miles and you wanna book yourself up into a lie-flat business class seat, for instance. Tinkering with your trip, continually working with it, uh, is the key. Um, I would say the, the first thing you need to do if you're thinking about getting into this kinda rebooking your travel strategy, which I always recommend you do, is booking the right fare.
What fares am I talking about?
Uh, like we just talked about, you know, those basic economy fares. You can't do this for free, or in some cases you can't do it at all. So giving, paying a little bit more for the flexibility to leave the door open to rebooking something if prices do drop or if a better flight comes up, if, you know, there's something nonstop that's a better price than what you booked with a connection.
Booking a main cabin fare or higher is the most important thing. I would actually say the single most important thing is just understanding that this is the piece of where you start to go full sicko mode, right? It, and this is where the importance of viewing this as a fun puzzle, of the endless pursuit of the best deal possible is actually something really fun.
And if you're listening to this and you're saying, "I wanna book it once and I wanna be done- This is probably the part where we lose you, but for everybody else, this is where it starts to get really fun, is that the booking process is, isn't over until that plane departs.
Yeah.
And that is actually really, really rewarding, not just in terms of having some fun with it if you do come to enjoy this stuff, but also, I mean, collectively, you and I, just by rebooking simple cash flights that we've booked, I bet we've probably saved $10,000, that we've pocketed $10,000 in airfare vouchers over the course of the last six years.
And if you apply that to, you know, we booked a flight originally and then rebooked something with points and miles, it's probably Multiples of that, right?
Yeah, definitely. I've saved so much money doing this. Y- I, I just wanna take everybody through my strategy here because it is pretty simple. Uh, the first thing you do is you book something that makes the trip work in main cabin or higher so that you have a flexible fare booked, but you know that you're gonna go on your trip if nothing else better pops up, right?
This, this is especially important if you know you need to be there for an event, or it's a group trip and you don't wanna have to bail at the last second. Book something that works that's flexible. Then I go into Google Flights, and I set a bunch of price alerts, not just on what I booked, but I set a price alert on everything that I wish I was flying instead, you know?
Whether it's the nonstop flight, or maybe a premium economy or a business class flight, or some different days or a better flight time. I just set, I go in and set alerts all over around my fare. And then finally, I set myself a weekly or monthly or, if I'm really feeling like a sicko, daily reminder to go and check on my travel.
Um, I, you know, I, I go in, I take a look at what I have booked. I go check what the price is now and see if I can rebook and get a better fare, and I check all those other price alerts to make sure that, uh, the f- the flight that I actually wanna take hasn't gone down in price, too. Um, in order to do this, I usually make a wish list of like, "What is my best possible routing here?
W- what's the flight I really wanna be on? What's the seat I actually wanna fly? Uh, what's the experience that I really want here?" And then I'll just go and check those things periodically. Because you booked that first flexible fare, you're covered. You're going on your trip no matter what, and it's just all gravy.
Then if something gets better, you can throw some points and miles at a lie-flat seat to make your, your trip to Croatia a little more comfortable, like I did a few years ago. That's exactly what we did. Um, my wife's friends, uh, from college all planned a group trip to Croatia, and we were all going. We were able to book flights that worked for us.
We were flying KLM. We booked main cabin flights that we knew that we could get a voucher for if we needed to cancel. And what I did was I started to set myself alerts to go and check that if there was award space to fly business class on United, which I knew that there was a possibility of. So what I would do is I would go and use my Air Canada Aeroplan miles.
I would go look every day or every week and see if that award space was there so that we could actually fly up front and make our journey over there a little bit more comfortable. Lo and behold, about three weeks before our trip, the award space popped up, and I used, uh, Air, Air Canada Aeroplan miles to book my wife and I into a United Polaris lie-flat seat, and it made the journey so much more comfortable, so much more fun and exciting to start our big trip, and we were able to cancel our KLM flights, uh, and get a refund there, too.
So it was, it, it ended up being like the perfect example of why this rebooking method works.
Yeah, having that wish list of the different alternatives, the better alternatives, whether it's more comfortable, quicker, cheaper, whatever Uh, it's just so important. Then you gotta decide on the cadence of how often you look for these things.
And I would say as that trip draws closer, maybe you're normally checking weekly, maybe a couple of times a month. The final month before departure, and especially the final weeks before departure, you probably ramp that up to weekly and then daily. Again, this is where you start to get into the sicko mode of constantly looking and hopefully rebooking, but the deals are worth it.
If you're willing to put in more work, you're gonna get a better deal.
Yeah. Um, all right. To close, in our last segment here, let's have some fun. I want you to do some myth busting, Kyle. Uh, some airfare myth busting. I know. I know this hurts you. This
hurts. It hurts. I'm gonna go to my grave bu- busting these myths-
and I just have to accept that, but it still hurts.
All right. We're just gonna get, we're gonna get hot reactions from you. All right? Here's, here's the first myth. To get the best deal, you have to book flights on Tuesday at midnight.
No. This is not a thing.
Where does this come from?
I have to assume it comes from a time probably somewhere around when you and I were born, when airlines were changing fares, like, on a weekly basis.
We live in a digital world that is governed by algorithms. Those algorithms are constantly changing airfare, not just by the day, but by the hour, and in some cases, by the second. Things are changing so rapidly now that there is just absolutely no truth to this. You are just as likely, if not more likely, to find a great deal searching on a Friday afternoon or a Thursday evening as you are at any time on Tuesday.
There's just no best time to book a flight, period. It does not exist.
Okay, the next myth. The airlines are tracking your searches, so to get the best deal, you should clear your browser cookies.
Get rid of those cookies, right? Who, who wants cookies? I want cookies because this is also bunk, for now. You know, in the last year or so, there has been a huge national conversation about airlines using AI and tracking your searches and adjusting prices to get more money out of you.
I can say definitively that right now, that is not what is happening. Airlines are not manipulating prices. They haven't done it before. They aren't doing it now. Might they do it sometime in the future? It's possible. We just don't know. Can't rule it out, but for now, don't waste your time with these kinds of things.
On the one hand, it's harmless to open an incognito browser or clear your cookies before you search. So if you, if you feel good about it, go ahead and do it. What I don't want is for people to view these kinds of things like booking on a Tuesday at midnight or clearing your cookies or using a VPN even as the ultimate travel hack and as, like, a sure, sure sign that you're gonna get the best deal possible when there are all of these other things that we talked about.
Booking flights on the right days that depart on a Tuesday, a Wednesday, or a Saturday, uh, using Google Flights, using Google Flights Explore, having flexibility and following the flight first rule. These are the things that really matter. These are the things that truly can save you hundreds of dollars or more per ticket Clearing your cookies isn't gonna do a thing.
Yeah. I would add to your list of the things that actually do save you money, uh, flying routes that have competition on them, I think that might be the number one thing, especially if Southwest flies that route, you're more likely to get a good deal. Southwest is still the number one driver of low fares in the United States, whether you like to fly them or not.
And like we said, a little flexibility, flying early in the morning or late at night, that's gonna save you hundreds of dollars sometimes compared to those middle-of-the-day flights that are a little bit more convenient. So get up or stay up to get the best price, too. Okay. At the end of every one of these Starter Kit episodes, we're gonna give you a flight plan or a to-do list of the big takeaways from the episode, the things you should get going on right now to start your award travel journey.
The first, if you want to outsource this work, if you want someone to do this for you, subscribe to our Thrifty Traveler premium flight deal alerts. Our team searches for deals for more than 220 US and Canadian airports to destinations all over the world, whether you wanna book the cheapest flight or use your points and miles to fly business class.
Uh, sign up today at thriftytraveler.com/premium and use the special promo code START to get $20 off your first year. Um, this next thing from the flight plan, Kyle, start thinking flights first in your travel planning. It's just the most volatile part of flight pricing. Get the best flight deal possible and plan the rest of your trip from there.
What's next on the flight plan?
Uh, booking quickly. You know, when you see a deal, book it. The hotter the deal, the shorter it lasts. Know that you've got this 24-hour rule. If you book a flight because you like the price or you love the price or you found a crazy mistake fare or you got something like that in your inbox, book now, ask questions l- later.
Ask those questions like, "Can I take this time off work? What do hotel rates look like? Can I book those? Can my spouse join me on this trip that I just booked a ticket for?" In some cases, is even the right order of operations for these questions, knowing that you've got the 24-hour rule. No matter what airline it is, so long as that flight touches US soil, if you need to cancel, do that within 24 hours.
You can get a full refund, get all of your money back.
Okay, number three on the flight plan, familiarize yourself with Google Flights and all of its features, the calendar, all the filters, the price alerts especially. Go bookmark Google Flights. Pour yourself a glass of wine. Spend an hour or two with Google Flights tonight.
I promise you it's gonna be fun.
So much fun. We're normal people here.
All right, last thing on the flight plan, Kyle, what do you have?
Uh, rebook and research and the booking process is never done. W- No matter whether you booked something earlier today or seven weeks ago, go set a Google Flights price alert.
Monitor those prices. If you don't love what you booked, whether because of the price or the routing or it's not in the right cabin that you wanted, make a wish list of the things that you would prefer to book. Make a, you know, a calendar or set some notifications for when to go back and check them. Keep working.
The booking process is never done. I promise the work is worth it.
Yeah. Uh, we're gonna put this flight plan into our show notes so you can go double-check it there and, uh, get started on your points and miles journey here. Also, if you wanna dive deeper on this topic, I've got one recommendation of a different episode of our podcast, and I wanna hear what you have to say, too.
But episode 72, which we actually recently recorded, How the Pros Use Google Flights, was really awesome, especially on YouTube. You can go and see exactly what we're talking about with all of those filters. Uh, that was a really fun episode and, uh, just a really great primer on how to get started with Google Flights if you haven't already.
What's your, w- what's your recommendation?
Well, you stole mine, so I guess I will also shout out an episode from earlier this year in 2026, our five-step checklist, what we do after booking flights. I mean, we really make the argument, which I think is really sound, that in many ways, the most important part of booking flights isn't actually booking them, it's what you do after to try to rebook and get an even better deal.
We'll have some other recommended episodes in the show notes as well. Kyle, I think all the listeners today are well on their way to becoming certified sickos like us. What do you think we should cover next time?
I think, you know, we covered the basics of finding cheap flights. Next is the basics of how to earn points and miles, what you need to know in order to earn the right ones.
Um, so that's coming next Tuesday.
All
right.
For now, thank you so much for listening to this episode of Starter Kit from the Thrifty Traveler podcast. Rate us five stars on your platform of choice, and like and subscribe to Thrifty Traveler on YouTube, where you can watch all of our episodes. If you're wondering what we look like, please keep your expectations low.
Uh, send this episode to someone you know who needs a vacation. If you have feedback for us, send me a note at podcast@thriftytraveler.com. I would love to hear from you there. Kyle, tell us about the team.
This episode was produced by your favorite host, the crown prince of Google Flights price alerts, Gunnar Olson.
Put that crown on, baby. This episode was produced and edited by Sylvia Thomas and edited by Kyle Thomas. Our theme music is by Benjamin Tissot. See you next Tuesday.
See ya.