106. Lessons Learned & Top Tips from Running Thousands of Award Searches

Welcome to Point Me to First Class, the only show for employed professionals, entrepreneurs, and business owners who are looking to optimize their higher-than-average expenses to travel the world. I'm your host, Devon Gimbel, and I believe that your expenses are your greatest untapped asset if you know how to leverage them. Ready to dive into the world of credit card points and miles so you can travel more, travel better, and travel often? Let's get started.

Hello everyone and welcome back to the podcast. If there is one thing I consistently get asked about more than anything else in the game of award travel, it's often this. How do I find great award flights? And this question comes in lots of different flavors like when should I start searching for award flights? Where's the best place to look for award flights? How do I increase my chances of finding award flights that are a great deal and also work for my travel schedule? What are the best tools or apps to help with award flight searches? No really, which single award search tool is the very best one? Usually followed by point.me, points.yap, seats.arrow, or insert any other award search platform here shows an award flight I want to book, but when I go to the airline website to book it, it is not there. What am I doing wrong?

These are just a few of the award flight search questions that I know so many of you have, and I can understand why award flight searches are the source of so many award travel questions. First, if you've gotten this far in this hobby, you've probably heard me or other points educators go on and on and on about how incredibly valuable your points can be if you learn how to find and book the best flight deals outside of your credit cards travel portal. But second, at least initially, that is much easier said than done.

Because searching for award flights, especially the ones that represent the best value and the biggest deals, is anything but obvious, intuitive, or straightforward. For folks who are great at earning points, but who have less time and enthusiasm for learning the intricacies of tracking down the hidden award flight deals, award flight searches is where travel dreams often go to die.

And on the one hand, while I do think it's fun and strangely gratifying to log into your credit card account and see hundreds of thousands or even millions of points staring back at you, the objective for most of us is not simply to stockpile points. It's to use them to create priceless travel experiences and memories. The only thing worth less than zero points are tons of points that never get redeemed. Especially if the reason you're not redeeming them is because you don't feel confident about running award flight searches.

And that's why today I want to dive into some lessons learned and top tips I've collected after running thousands of award searches over 10 years for myself and countless students and clients. Award flight searching is a huge, broad topic that could easily be a podcast all on its own. So we're not going to be able to cover everything in a single episode, but what I do want to provide you with today is a high-level view at some concrete things you can do to improve your own award flight searches by highlighting high-yield practices and recommendations for setting up successful award searches.

Some of these tips are going to address the mental game behind award searches, and other tips are going to be more specific, granular things that you can put into action starting with your very next award flight search. My hope is that you walk away from today's episode with at least one actionable step that you can take to improve your award flight searches from now on, whether you're about to run your very first or your 100th flight search.

In no particular order, I have five award search lessons that I've learned from running thousands and thousands of flight searches that I want to share with you today. But before we dive into that, let's talk for a minute about why running award searches can be challenging.

First, running a search for flights that you can book using points is very different from running a search for flights that you can book using cash. And I know that may sound really obvious, but it's still important to state that. Up until getting into points, many of us have booked flights one way. We go to Google flights or we go directly to the website of our airline of choice and we type in where we want to go, when we want to go there, and then we're shown one comprehensive list of all the flight options that we can choose from depending on our preferences for itinerary and price. Easy peasy. You run one search, you review all the options available, you pick your favorite, and you book. Then you're done.

Running award flight searches does not look like that. Up until about two years ago, there was no online search platform analog of Google flights where you could input in all the same travel info and get one comprehensive list of all the points flight options available across all the different airlines or booking programs using any one of the many points currencies that are available.

Now that is starting to change with award search platforms, many of which have gotten increasingly robust and comprehensive over time, but there is still no single one-stop shop online that is going to do an award search for you completely. In an upcoming podcast episode, I'm going to do a deep dive into the difference between using online search platforms to run award searches versus running manual award searches. But for today, just know that a current challenge of running award searches is that we still don't have an exact replica of Google flights when it comes to looking for points flights. And what that means is that you have to develop new skills in order to run successful award flight searches. But the good news is that you are all way more than smart enough to do that.

Now, the other reason that running award flight searches can be challenging is the obstacle of information overload. It used to be that folks could not maximize the value that they could get from their points by booking award flights because there just wasn't that much information available about where to look for great points flight steals or how to run award flight searches. But now we have the opposite problem. There are hundreds if not thousands of blogs, podcasts, Instagram accounts, and who knows what else, sharing award travel information and tips. And I'm willing to bet that the vast majority of those are sharing great, useful information. But it's so much information to sift through and make sense of and know what to rely on and when. Especially if you're an information gatherer who loves learning and wants to have all the facts in front of you before you start trying to do anything, you can easily find yourself stuck learning more and more and more about award searches without actually getting any better at running them. So we're going to change that starting today.

The best news is that you don't have to run thousands of award searches over the next few years in order to start getting better at them, because I've already done that work. Instead, I'm going to share five actionable tips to make your award flight searches easier and increase the chances that you find the dream flights you're looking for. Consider these tips the foundation that help set you up for award flight search success. More specific, granular advice can always be added and titrated to your specific travel preferences, but what I'm going to share with you today is the base knowledge and mindset to apply to all of your award searches going forward.

So let's start with some search logistics that can make all the difference. Award flight search tip number one is to run one-way award searches even if you're traveling round trip. What this means is that when you're first searching for award flights for a trip, do not run a round trip award flight search even if you are traveling round trip. Instead run a one-way flight search just for your outbound flight and then run a totally separate award search for just your return flight.

Here is what this could look like. Say that you want to fly from Dallas to Rome for a one-week vacation in the fall. Don't search for a round-trip award flight from Dallas to Rome and then back from Rome to Dallas. First, run an award search only for the Dallas to Rome flight for your days of travel.

Why do this? So there are a couple of reasons why I always run one-way award flight searches. First, it increases your chances of finding potential award space. That's because if you run a roundtrip award search, there has to be award availability for the number of tickets that you're searching for on both legs of a roundtrip itinerary in order for you to get results for that search.

If a given airline has award availability on only the Dallas to Rome leg of the journey, but there's no award seats open on the return Rome to Dallas leg, your round trip award search will just come back completely empty. All it will tell you is that there are no award seats available that match your search parameters. It won't tell you that there are award seats available for the outbound leg of the journey but not for the return leg.

So do yourself a favor and always run one-way award searches. This will ensure that you don't miss any potential award availability for either of the legs that you're traveling. Now you might be wondering, but isn't it cheaper to book a round-trip itinerary versus two one-way itineraries? And this is certainly true for booking most cash flights, but for the most part, this is not how award flights are priced.

Many many award booking programs will charge you one half the points cost of a round-trip award flight when you book a one-way award flight, meaning that there's no savings or cost difference to book two one-way award flights versus a round trip award flight through the same airline program.

Notable exceptions to this rule are Emirates and American Airlines, which can price out round trip award flights cheaper than the cost of two one-way award flights. But my advice remains the same. In terms of running searches, first run your award searches as one-way flights. If you find both an outbound and a return one-way flight available to book through a single airline program, then you can run a round-trip award search just to make sure that you're not missing a better points deal by booking a round-trip itinerary.

The majority of the time, it's not going to be cheaper to book a round-trip award flight, and the key here is that first you want to increase your chances of finding available award flights by running one-way searches.

The second reason that I love running one-way award searches and why I recommend it is because this approach allows you to expand your potential award options beyond just one airline program, or even beyond the transfer partners of just one points currency if you happen to have access to points in multiple points ecosystems.

So let's say that you have miles in American Airlines, you have Chase Ultimate Rewards points, and you also have Capital One miles and you're searching for that flight from Dallas to Rome. So you take my first piece of advice, you run a one-way award search from Dallas to Rome on the American Airlines website and you find a flight that works for your schedule that charges 19,000 miles for a one-way economy flight.

But when you run a search for your return flight on American Airlines, American doesn't show any options available. Now in this scenario, this is not a huge problem because you have other points and miles that you can use, which means that you have other airline programs that you can search for potential award flights for your trip home.

Because you also have Chase and Capital One Miles, you run a search for award flights for your return leg and find a flight coming home on Air France for 25,000 miles, and you find another option coming home on Iberia for 29,000 points or miles. You can use either your Chase or Capital One miles transferred to Flying Blue to book the Air France flight, or you could transfer points to British Airways or Iberia to book the Iberia flight if you just like paying more in points and taxes and fees. The point is though that running one-way award flight searches not only increases your chances of finding award availability, but it also allows you to expand your award flight options to as many airline transfer partners as possible based on the specific points types that you have access to.

You cannot mix and match a round-trip flight itinerary between entirely different airline programs when you book a flight using cash, but a huge benefit of using points is that you can book an outbound flight on one airline and a return flight on an entirely different airline thanks to the fact that most programs will price award flights at half the points cost of a round-trip flight.

Now the third reason that I recommend running one-way award searches is because of increased flexibility and increased options, both in terms of potential routes, but also so you can mix and match different classes of service for your outbound and return flights. If you don't want or need to fly the same class of service both ways.

I know many people who are comfortable flying economy for daytime flights between Europe and North America, but who prefer to book premium economy or lie flat business class seats for overnight flights that typically run from North America to Europe.

Running one-way award searches allows you to find and book flights in different classes of service, creating an itinerary that's even more tailor-made to your travel preferences. It also gives you expanded options of potential routes if your preferred route is not available.

Let's say that you found a great award option for your Dallas to Rome flight, but you don't find any return Rome to Dallas award flights that work for you. When you search and book award flights as one ways, you can expand the route options to include nearby airports that you're also willing to fly from on either leg.

So even if a return flight specifically from Rome to Dallas isn't available, you might find an award option that returns from Venice or from Milan. You'd never find these additional options if you're only running round-trip award searches for all of your flights.

But now let's talk about actually booking a round-trip award flight itinerary versus just running one-way award searches. This is just a bonus tip, but I briefly want to talk about whether it makes sense to book two one-way award flights versus outright booking a round-trip award flight in the scenario where you're flying into and out of the same city pairs, where you're flying the same class of service on both legs of your itinerary and where you do manage to find award availability for both legs of your itinerary through a single award booking program. In that case, isn't it easier and preferable to actually book the award as a round-trip itinerary?

Now, I would still say no for the simple reason that assuming there's no price benefit to booking a roundtrip award flight over two one-way award flights, booking your itinerary as two separate one-way awards increases the flexibility that you have. If you need to cancel or change one of your two flights, it's so much easier to do that when you've booked them initially as one-ways rather than as part of an inclusive round-trip itinerary. You have more freedom to cancel a single one-way award and find an alternate option if you need to change your travel date, for example, versus having to cancel an entire round-trip itinerary when only one of your travel legs really needs to be changed.

So do yourself a favor, search for and book your award flights as one-ways unless you have a compelling reason to book them as round-trip itineraries.

Alright, let's move on to award search tip number two, and that is know when award booking calendars open and use that to your advantage. Did you know that different airlines open up their booking calendars at different times? What that means is that some airlines will allow you to start booking flights 331 days in advance, for example. Other airlines will allow you to start booking flights as many as 350 days in advance. And there are yet other airlines that will let you start booking flights as far as 360 days in advance.

So let's pretend that today is January 1st. Say that you wanna book a flight from Los Angeles to Tokyo for December 27th, which is 360 days in the future. You might start by going to the American Airlines website, but you quickly notice you cannot search for a flight on December 27th because American Airlines only allows you to book as far out as 331 days in the future.

So the farthest in advance that you could search for that LA to Tokyo flight would actually be November 28th. Instead, you'd have to wait another 30 days before American Airlines will even let you search for that flight on December 27th. But you do have other options, because other airlines let you book flights farther out than just the 331 days that American Airlines allows.

You could instead head over to the British Airways website, which opens its booking calendar 355 days in advance. Again, if we are sitting on January 1st, we wouldn't be able to search for flights from LA to Tokyo for a December 27th travel date, but we could look for flights for any travel date up to December 22nd, because BA opens its booking calendar 355 days in advance. Now if we really wanted to book that December 27th flight, we would have to wait a few more days until January 6th to be able to search for it through British Airways.

But we're not stuck because we could also go over to Cathay Pacific's website and actually search for that December 27th flight as early as January 1st. And that's because Cathay opens its booking calendar 360 days in advance, a good month before American Airlines will even let you search for flights.

And when it comes to award flights, this can matter. It can matter a lot. Oftentimes with the most coveted award flights, whether that's a specific route that's in really high demand or an itinerary in a premium cabin like International Business or First Class that tends to get scooped up really quickly, the early bird gets the worm. And if you can position yourself to find and book award flights before other airlines even allow you or other people to search for those same flights, you can be that early bird.

Imagine that you have access to several different points currencies that would allow you to book award flights through American Airlines, British Airways, and Cathay Pacific. If you're being strategic about your award search, you'd be ready to find your potential dream award flight on the Cathay Pacific website 360 days before your ideal travel date. This is going to be five days before British Airways would even allow you to search for that same flight and a full month before American Airlines would allow you to search for it.

Knowing how far in advance specific airlines and award programs open their booking calendars is a master move in positioning yourself to have first dibs on the best award flights. But don't worry, you don't have to magically know this or search around the internet to find out when the different airlines open up their award booking calendars. I've created a really simple award calendar chart that tells you exactly when the main award booking programs open their calendars and how far in advance you can book award flights. And it's totally free for you to download. Just click on the link in the episode description or the episode show notes, and I will email you your own airline award calendar chart that you can save and use as a reference for your future award searches.

Okay, back to the flight award search tips. Coming in at number three is the most broad, but truly I think the most important recommendation that I can give you to increase your chances of award search success. And that is that flexibility is key. That is truer now than it has ever been. So let's look at what this means and why it is crucial to expanding your potential award flight options.

I've already mentioned one major way that award flight searches differ from searching for cash flights in that there's currently no one comprehensive award flight search site that is analogous to Google flights. But another important way that award flights differ from searching for cash flights that is definitely going to impact you and potentially significantly hinder you if you don't know how to navigate around it is inventory.

If an airline has an available seat on any given flight, they're going to let you pay cash for it. That might be a very, very high cash price, but they're still going to be willing to sell it to you. The same is not true of points flights. Just because an airline has open seats on a given flight, whether that's economy seats, premium economy seats, business class seats, or first class seats, that does not mean those seats will be made available to book using points.

I'm sure that every airline has their unique formula for deciding how many seats in which specific cabins they make available to book using points at whatever certain time points. And while those formulas are a mystery to the vast majority of us, one thing that you can count on is that airlines limit the number of seats they release that can be booked with points.

This is particularly true of premium cabin seats, especially on long-haul flights, especially to high-demand destinations, but this really applies to all flights. Again, just because a seat is available to book using cash does not mean that it's going to be available to book using points. Or if it is, that it's available for a reasonable number of points. So what this means for your travel planning and how you approach searching for award flights is that you cannot expect to get everything you want when you're booking points flights. Points are amazing, but they're not perfect and they're not a panacea.

So here's what to do if you want to increase your chances of award flight search success. Before you even begin running award searches, make a list of your top itinerary priorities and decide what you're willing and able to compromise on and what you're not. For the average award search, these are the five travel parameters that I'm talking about.

Number 1, destination. Number 2, route or itinerary, including whether you prefer to fly nonstop or you're willing to book a connecting itinerary. Number 3, the dates of travel that you would like to travel, number 4, the class of service that you want to travel in, and number 5, the points price that ideally you want to pay.

So start out with your ideal wish list of travel parameters. Here's what this could look like. Let's go back to that example of someone wanting to fly from Dallas to Rome. Your award flight wishlist could include that you wanna fly from Dallas to Rome, ideally flying out on a specific Saturday in September and returning home the following Saturday. Since you only have a week of vacation, you would like to fly nonstop to minimize travel time. You also want to fly business class and you want to book one-way flights for 75,000 points or less each way.

I don't think that there's any harm at all in running an award search trying to find a flight that gives you everything you want. That is a great starting point because if you find an option that ticks all of your boxes, fantastic! Book that thing before it disappears. But if you've ever run an award flight and you haven't found that perfect option, don't give up and don't get discouraged.

In fact, please hear me when I say, finding an award flight where you get everything you want is oftentimes the exception, not the rule. So your travel wishlist is a starting point for your award flight searches, not necessarily the ending point. If you run an award search and don't find an option that hits all of your criteria, this is where my tip to be flexible comes in.

Just like I said to create your ideal travel wishlist before you even start searching for award flights, you also wanna have an idea of which of those travel parameters you can be flexible on and how flexible you can be. Where are you willing or able to compromise on your travel wishlist if it means the difference between having no options for award flights versus finding a pretty good fit option.

Can you look at connecting flight options instead of just non-stop itineraries? Can you shift your travel dates by a little or even by a lot? Can you position to a larger airport or an airport with more flight options instead of flying from your local airport? Or can you be flexible on your arrival airport? Are you willing to pay a higher points price to book an award flight that otherwise meets all of your ideal travel criteria?

If you're trying to book flights for a group of more than two people and you can't find any decent award options, can your party split into two groups to increase your chances of snagging award availability? Perfect is the enemy of amazing when it comes to award flight options. So please do not sacrifice finding an amazing award option because you're expecting to find something perfect.

Instead, know where you can and where you can't compromise on your search parameters. And as long as you have some flexibility, your chances are good that you're going to find one or more award flight options that are great contenders.

This is a great time to also mention that while many of us love a great points deal, getting a low-priced award flight or scoring a sky-high redemption value from your points is not the end-all-be-all marker of using your points well. If you find a redemption that makes you happy, you've done the math and you're satisfied with the redemption value that you're getting from your points, and your points are allowing you to travel more or travel better than using cash alone. That's a points win.

All right, let's say you followed all of my tips so far on an award search and you're still coming up empty handed.

You've run your one-way award searches. You were prepared to start your searches at the right time based on award booking calendars opening, you know your areas of travel flexibility, and you've run searches that incorporate that flexibility, but you still haven't found award flights that will work well enough for you. What then? That's where award search tip number four comes in handy. And that is, don't be afraid to set award alerts if your initial searches don't reveal award options that appeal to you.

Flight award space is dynamic. That means that it can and does change over time. Just because you're not finding a great fit award flight when you initially run a search, doesn't mean that it won't pop up sometime later in the future. Some of you don't have the ability to book flights the day that award booking calendars open, so you can't search for flights when they immediately become available. Some of you can, and you find award availability, but all the flights might be priced at an unreasonably high amount of points that you don't want to pay. So some award searches are successful the first time, but not all of them are, and that doesn't have to be a problem.

Many award search platforms or online award search websites offer the option to set an alert for a specific flight so that if award space becomes available on that flight in the future, you can automatically receive an email or a text message alerting you and then you can jump online to book that award flight. Now you'll get the most functionality setting award alerts in terms of how many alerts that you can set and how detailed search parameters you could include in your alerts if you have a paid subscription to one of the award search platforms that offers alerts. But several award search platforms also offer limited flight alert functionality on the free versions of their product.

If you don't have the time or you don't enjoy the process of searching for award flights, or if you wanna receive notifications when specific flights become available, investing in an award search platform, even for a month-long subscription, in order to access flight alert functionality can be highly valuable. And just in case you're wondering what award search platforms I like best and how to choose which one or ones will be most useful for you depending on what you're looking for a search platform to do for you, stay tuned. I'll be doing an award search platform deep dive of its own podcast episode soon.

But that brings me to my fifth and final award search tip for the day. And this is something that you're going to want to know about because even a successful award search can go south quickly if you don't keep this in mind. And that is, don't forget about points transfer times and plan accordingly.

One of the keys to getting maximum value from your points for flights is to transfer them out of your credit card account and into an airline transfer partner account of your specific points currencies and then to book your flights directly from those frequent flyer accounts. But there are a few nuances of transferring your points that you absolutely need to be aware of.

First, points transfers are one way and irreversible. That means that once you move points from a credit card account to a specific airline or hotel transfer partner account, those points now live in that airline or hotel account until you use them. You cannot change your mind and send them back to your credit card account. You can't decide that you want to send them to a different airline or hotel account and then move them again. You can move them once and that is it. Points transfers are one way and they're irreversible.

The second thing that you need to understand about points transfers is that while many transfers are instant, some are not. For many airline programs, you can log into your credit card account, initiate a points transfer to a specific airline where you designate exactly how many points you want to transfer over, and those points get moved instantly. You can log in to your airline frequent flyer account a few seconds after you set up the transfer and you can already see the points or miles in your account and use them to book a flight.

That's very convenient because it means you can leave your points safely in your credit card account until you have searched for an award flight, confirmed one exists that you actually want to book, and then you can transfer your points over from your credit card account and ideally book your award flight immediately.

But some credit card to airline transfers are known to take more time. American Express points transfers to ANA, for example, are known to take two to three days. Chase points transfers to Singapore Airlines can take 24 hours. Other times, points transfers that are usually instant can uncharacteristically take a few hours, a few days, or even a week or more to finally land in your transfer partner account.

This matters because even if you find a great award flight that you want to book, it's not yours until you've actually booked it. If a points transfer to your airline account takes hours or days, your dream flight can get booked by someone else while you're waiting for your transfer to complete. While we can't predict if any given points transfer randomly takes longer than usual to complete, you can put yourself in the best position to book great award flights by familiarizing yourself with average transfer times of your points currencies to specific transfer partners and use that information to your advantage.

For example, say that you are sure that you want to use Amex points to book an award flight through ANA even though ANA hasn't opened up their award calendar yet for your dates of travel. You also know that ANA award tickets can get booked fast on the day that they're released and that points transfers from Amex to ANA regularly take two to three days, so you don't want to wait to find your ideal flight and then risk that flight getting booked by someone else while you're anxiously waiting your points transfer over from Amex.

You can prospectively transfer points from Amex to your ANA account the week before you intend to start searching for award flights just to ensure that your points are ready and waiting for you in your airline account so that you can book an award flight immediately once you find one that works for you. Now I did say earlier that points transfers are one way and irreversible. So this strategy should only be used if you have a very high level of confidence that you're gonna use those transferred points to book a flight before their expiration date, which in the case of ANA is 36 months after you first transfer your points.

But if you're more conservative and you don't feel comfortable transferring points prospectively, that's fine. There's still another option that's potentially available to you, which is that some airline programs allow you to put award seats on hold so that they're safe while you're waiting for a points transfer to complete. Not every single airline offers this, but it is worth calling to see if you can put an award flight on hold if your points transfer is not instant or immediate. All you have to do is have the specific flight details of that flight that you wanna hold and provide that information to the airline representative when you call. And they can set up a hold of that award for you if it's available.

All right, everybody, that's it. Five tips to set you up for better, more successful award flight searches. I hope that one or more of these tips makes your next award flight search easier, but more importantly, helps you find and book incredible points flights for your next adventure.

However, this episode really has just started to scratch the surface of how to run successful award searches. And one of the challenges of running a podcast is that there are limitations to what I can show you, literally, given that this is an audio only format, and also how much of what I teach is tailored to you specifically, because I don't have the chance to work with you individually.

I do my best to provide broad, actionable tips and strategies that I hope are applicable to as many of you as possible. But I also know that you may have tried running award searches before and still gotten stuck. You might be searching for more hands-on help, more detailed award search processes to follow, or you may want to fast-track your ability to earn and use your points for maximum value so that you can stop stockpiling your points and start booking that long haul business class flight or overwater bungalow of your dreams.

That is why I created Points Made Easy. It's my online course and I want to invite you to join it when enrollment opens again in just a few weeks from March 22nd to March 30th, 2025.

Inside Points Made Easy is where you'll find my step-by-step award search process, your roadmap to finding the best flights bookable with points. You'll get hands-on personalized help from me crafting your perfect fit credit card portfolio and you'll get tutorials for when and where to use those points to book your dream trips.

You'll also get exclusive access to award booking workshops where I help you find your dream awards and I teach you how to do the same thing so that you are set up for award booking success for your next trip and all of the trips after that.

If you're looking to accelerate your points proficiency and you want to work with me to make earning and using points even easier, you're invited to join the Points Made Easy course when it opens for enrollment on March 22nd. I only open this course once or twice a year and it's the only place that I work personally with clients. So mark your calendars and join the waitlist for the course today.

You can find that at https://pointmetofirstclass.com/pointsmadeeasy. In the meantime, have a fantastic week, everybody, and I'll see you back here next time.

Thank you for joining me for this week's episode of Point Me to First Class. If you want more tips on turning your expenses into travel, visit pointmetofirstclass.com to learn more. See you next week.