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If you had to fit the core principles of maximizing point redemptions on a three by five index card, what would it say? Well, I got that question from a listener named Matt and I loved it so much I'm going to build this entire episode around it. But I'm not going to just stop there because I'm going to take a dozen of your questions about booking travel with points and miles and organize them
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into a walkthrough of the entire process, end to end. Not just the theory, but the actual steps answering your questions along the way.
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So it's kind of like an AMA episode as well.
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We'll cover why the same business class
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seat can cost 240,000 miles or 64,000 miles, depending on how you book it and what to do when a route looks impossible to find. Availability. I'll share how my thinking on travel portals has evolved.
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We'll talk about domestic flights and how
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things change there and whether it ever
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makes sense to use your points to upgrade.
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Whether you've never transferred a point in your life or you're deep in the game. I really think there's going to be something here for you. But fair warning, by the end, you might need a magnifying glass and very tiny handwriting to fit everything we cover on one index card. Like Matt asked, I'm Chris Hutchins. If you enjoy this episode, leave a comment or share it with a friend. And if you want to keep upgrading your money points in life, click follow or subscribe all right, before we get any further, I think we need to understand the fundamental mechanic that makes this whole points and miles game worth playing. I've talked about this before, but I'll just say briefly, there are two primary ways you can use your credit card points for travel. Option A is kind of the easy mode, which is oftentimes we get targeted to do is to just use the travel portal. You go to Chase Travel, Amex Travel. You search for a flight the way you'd search on Google Flights. You search for a hotel the same way and you just pay with your points instead of cash. It's simple. Your points are worth somewhere between one and one and a half cents depending on the program and the portal. And with Chase's new points boost system, you can occasionally get up to 2 cents, but definitely not always. So if a flight costs $500, you're going to spend 25 to 50,000 points. It's easy. There's no learning curve done. And honestly, it's not the worst option out there, right? You could be redeeming your points for gift cards or you could let them expire. So there are way worse options. Option B is that you transfer to an airline or hotel loyalty program. You can move Chase, amex, Capital One, Citi, Bilt, Wells Fargo, all to different airline and hotel groups like Air Canada, aeroplan, British Airways, Hyatt, Air France. And you can book award flights air in that program at that program's prices. And that's kind of where the magic happens because airline award charts are often completely disconnected from cash prices, though that's changed a little bit.
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And it's possible sometimes to get 2
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to 5 cents per point and sometimes even more than that. So if you look at an example that I gave in episode 238, and by the way, if you're ever trying to find any of the episodes or resources we mentioned, take a look in the show notes or for episodes you can just go to allthehacks.com 238I highlighted a flight from Boston to Amsterdam on on Delta in business class and the cash price was $2,700. And on Delta using Delta Sky Miles, it was 240,000 miles plus $6 in fees. But you could book that exact flight through Air France's program flying blue for 64,500 miles. So almost a quarter of the number of miles you need. It was $33 in fees instead of $6 in fees. So pretty negligible. So a much better deal. You could even book it for less at 47,500 miles with Virgin Atlantic miles. But there is almost $1,000 in fuel surcharges. So I'm going to argue that that's probably not the right choice for anyone. It's the same plane, it's the same seat, it's the same flight.
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But depending on which program you book
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through, the price can range wildly 5x difference. And flying Blue and Virgin Atlantic are both transfer partners of almost every single points program. So almost anyone with points can access deals like this. So why does this work? Well, airlines are selling miles to the banks for revenue, and a lot of these foreign airline programs don't have access to American customers because we're unlikely to get an Air France or a Virgin Atlantic or an Air Canada card because we just don't fly that airline enough. But if our transferable points can go to those programs and book with them or their partners, even if it's just for one flight a year, that gives them access to us. And they're excited about that. And we're excited because a Lot of them have sweet spots that, that are really exciting like the one I just talked about. But at the end of the day, you're still booking a Delta flight. And in many of these programs, you're not earning that many points or status qualification from award flights. And so whether you book that United flight through Air Canada or through United, it's not that different. Now that has changed a little and some of the US airline programs will give you some qualification towards status, but it's not usually as much as if you paid for the flight with cash. And the trade off in terms of the deals you get, booking with flights can be so worth it. So a real world example here is that a listener named Jody wrote in and said she's gotten a ton of points on her Hawaiian cards and doesn't want to fly to Hawaii all the time. Well, great news, Jodi. There are a lot of options. So because Hawaiian merged with Alaska and they now have the ATMOS program, you can book all of those partner airlines. And Alaska has a ton of them. Not just the one world partners like American Airlines, British Airways, Cathay Pacific, but they're also partnered with Condor to get to Europe, Emirates, Iceland Air, Fiji Air. There are a lot of other partners you can book just from the ATMOS program. So I want to encourage everyone to kind of separate the idea of British Airways points being for flying British Airways. And just think of there are a ton of different places you can book your flights and they all have different partners, some of which are within and some are outside of an alliance. And so yes, that can be confusing and stressful to think about because there's just so many options. But, but we're going to kind of simplify that in this episode. One catch with all these transfers is that you can't reverse them. So once you move your points from Amex to Air France, they are Air France miles. You can't reverse it, you can't transfer it back. You might in some programs be able to transfer them to someone else, or in many programs you can book for other people, but you're not going to get those miles back in Amex or Chase or Wells Fargo. So definitely want to make sure that you understand the program. You find the availability or you know it really, really well before you're making those transfers. But, but most of those transfers are really quick, instant seconds later. Sometimes you have to log out and log back in, and in a few cases they take a little longer, but in almost every case they're very, very fast. And because of that, I Always try to find the availability and then make the transfer. But that's getting a little ahead of ourselves. Let's start with just defining the trip, because I think this would be a big, big part of that index card. Because when you sit down to think about planning a trip and you want to use your points, I don't want you to start by just opening an award search tool. The only exception to that is if you just have a bunch of points and you don't care where you go or when you go and you have ultimate flexibility and you just want to find some awesome place to go. Great. Open an award search tool you can go back and listen to. I think it's episode 166 where Greg from the Frequent Miler and I went through all the different award search tools and there's all these great discovery tools where you can actually just find flights with ultimate flexibility. So that is definitely not a bad idea if you have that flexibility. And I'm going to assume you don't, because most of us don't. But what I do think you need is some amount of flexibility or some amount of luck. Sometimes the exact thing you want is available and sometimes it's not perfectly, but you want to think about. Okay, here's this trip I'm taking. Where am I flexible? Because where you're flexible, you might be thinking, oh, flexible is always dates. And that's not the case. Dates is a big one. Can you shift it by a few days? Can you shift it by a week? Or are you locked into school breaks? Are you flexible with your destination? Is it somewhere in Europe or is it, we have to get to Paris? Are you flexible with the routing? Are you willing to just fly to Frankfurt and buy a cheap other flight or take a train to get to Paris or Zurich if that's where you want to go? Are you flexible on your cabin? Do you only want business class or would premium economy or economy work? When are you going to book? Are you willing to book this or do you have the time to book this 12 months out, or do you want to book it three months out? How far in advance are you planning this trip? And then this is one that most people don't love, but I'll give a great example of this is are you willing to split the party if you have two kids and two adults, Are you willing to fly one adult and one kid on one flight and one adult and another kid on another flight? Now, I have booked that for our family and in every time it's happened, we've not had to take that flight for reasons I'll talk about later in terms of things evolving and the more flexibility you have, the easier it is to find great deals. So when we wanted to go to Japan, we weren't flexible on the dates because we were trying to go over a school holiday. So we didn't have a lot of flexibility there. But we were flexible on where we flew from. And so would we have to fly direct from San Francisco? Could we fly to la? Could we fly out of Seattle? And would we be willing to split up? So originally we found two seats flying from San Francisco to Narita and two seats from San Francisco to Haneda, both Tokyo airports, both leaving around the same time on the same day. And so because of that we booked those things separately and eventually we actually found what we wanted later. But I'll get to that. And so that's something I want you to think about. That goes on the index card. Where are you flexible? And those are the options. And so that's the first thing I'm thinking about when I'm thinking about booking an award trip because it really changes what you do.
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And then the second thing is you want to define what you're actually looking for. And so this is what I think a lot of people skip. And it's probably the top mistake I see in emails where people are sending me a message saying, gosh, I can't find anything to go from point A to point B. Are these miles not worth anything if I can't use them for the trip I want to take? And not all the time, but many times the challenge there is someone is searching from their home airport all the way to their destination, not realizing that there are very few airlines that have themselves or with their partners for flights from all of those cities connecting. And so just the other day someone posted in our member community about trying to figure out how to get from Phuket in Thailand all the way to Miami. And unfortunately they had a flight routed through the Middle east and given everything that's going on, they were looking for another option and there were just nothing. If you searched even on Google flights, there were very few options, you know, the week they were looking. But if you just looked on Google flights, just as an example for flying from Bangkok or Singapore or Kuala Lumpur, there were so many more options and there are tons of flights from all three of those cities to Phuket. They might be on AirAsia or carriers that are local to that market that don't have any partners that fly across the ocean. And so if you search for you Know, Miami to Phuket, you're not going to find a flight that connects with an airline that doesn't have a partner that can get you from Miami to that connecting city. And so I think that's really important, especially if you're flying to kind of smaller destinations. An island in Greece, a small city in India, somewhere that's not Bangkok or Singapore or Hong Kong or Tokyo. But that example for Phuket, it doesn't just have to be small cities. So we got a question from Carrie, who said she's planning a trip to Thailand. She wants to use Capital one miles. And so she was thinking EVA Air is a transfer partner. A and A. You could book through aeroplan. And I would encourage you to think it's not just US to Bangkok, because there aren't US to Bangkok flights. There might be one from la, maybe. So, yes, she was thinking, okay, I could go through Taipei or I could go through Tokyo, but you could also go through Hong Kong, you could go through Singapore. In a different time, you might consider flying through the Middle East. You could even probably fly through Europe. So the search isn't US to Bangkok. Typically, how I would think about this is the search is us to somewhere in Asia maybe is probably the first search I would consider. And you could do that by searching multiple cities. Some tools let you search for different regions. We'll kind of come back to that. And then once you get to that city, you can find a connecting flight. That's pretty easy. And similarly, we just booked a trip to Europe and we were trying to get to Switzerland. And even though there are major airports that fly to the U.S. many different cities in Switzerland, there were no flights, but there was a flight from San Francisco to Frankfurt. And. And so when I'm kind of thinking about this, I'm often using a tool called Flight Connections, which, you know, you can go and search this airport and see all the direct flights. And as a lot of these award tools are evolving, they're including searches from regions. And so we'll talk about that also. But I'd encourage you not to think about just the start and the finish is the only things you're searching for. It's often region based. Maybe it's you want to search from five airports on the west coast to six airports in Asia that you know have direct flights and see what you can find there. And then about when to book it is another important question before you kind of jump in. And Frank wrote in a while back, so apologies, Frank, I did not get to this question. Soon enough. And he was looking to book a trip to Europe and said, how do
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I think about planning this?
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And so the first answer is, as soon as you think about a trip, you should start planning it. The reason for that is that many programs release their inventory kind of somewhere between 330 and 361 days out. So if you're planning a trip and you are more than one year out,
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you have the ability to plan as
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soon as the schedule opens. Now, there's no tried and true rule for how many seats on how many routes every airline releases. So I'd encourage you to kind of do some searching, do some homework, and you'll find that some airlines right when the schedule opens, release two or four seats. And so you could just be like ready to go. There's definitely a post online somewhere about every kind of airline and what time that releases in what time zone. And you can go in, just book that. And so that's one option. And I would encourage anyone who's thinking about doing that to kind of start a week early and just practice what it's like to get on their website, find the inventory, kind of get ready to go and all that. If you are trying to travel in peak times and you're trying to do in business class and you're trying to do it direct and you're not 12 months out, well, then the answer there is really, you've got to be flexible. Now, historically, it's actually the other easy time to book has been really close to departure in the two weeks before departure. I found that that's not as consistently available as it used to be, and that the real answer is airlines are constantly releasing availability, but it's not always when you want. And so almost every trip we've taken in the last five years, we've we found flights that are very good for what we want direct, almost always, sometimes one stop in business class for multiple people. But if you only judged whether we were able to find inventory on the first day we searched, it would look very unsuccessful. That happens so often. So I will get to that. But high level, if you can book a year out, great. If you can book last minute, I wouldn't wait for it. Because one of the important things to remember is that a lot of these programs let you cancel flights booked with miles up to as late as departure. I think it's United lets you cancel after departure and for a penalty, you can even get your miles back. I would encourage you to do that and I would encourage you to read all the rules, because there are rules for every program about their award cancellation policies. But if you already are sitting on miles in a program like United or Alaska and you don't have to transfer to them, if you find something that just kind of works, you could just book it and know that you can cancel it later. So the thing I'm always doing is I'm looking, and as soon as I find something that will work that I'm comfortable doing, I will book that. If I have to transfer points to that program, I'll probably put a little more thought into it just to make sure I'm not transferring to some obscure program where points and miles expire really quickly and that I'm going to get stuck or that only has one particular use case. If the flights are kind of fine and adequate but not perfect. But if the flights are great, I will do that, no problem. Or if it's a program that I know really well, or if it's a program where I already have the miles. So for example, I've taken advantage of some of the built transfer bonuses to Avianca, Life Miles and Air Canada. So I already have miles in those programs. Air Canada is a little easier to cancel than Avianca or at least a little cheaper in many cases. And so if I saw a flight that was pretty good, I would just book it out of those programs because the miles are already there. And. And if it's reasonable and the cancellation fees aren't crazy, then I'll book it. And if something else great comes up, then I can just cancel it. And if not, I already have it. So the best time to look for those flights is whenever you know that you're gonna take them. As long as that's within a year. Otherwise it's at 330 to 361 days, depending on the program. So how do you actually do that looking? Tracy wrote in and said, how do you find a board space? That's what I'm struggling with the most. And I totally understand that this can feel overwhelming. Cause there's lots of tools and lots of routes. So I'd encourage people to go back and listen to episode 227 with Devin Gimble where we kind of talked about the Dunning Kruger framework for kind of learning and how it might start off really exciting and then get really stressful when you learn a lot and then you kind of come out of that. And so I would encourage you to first understand that that's normal. And then second, just start with one tool or one program or One trip and don't try to master it all. If you want to pick a program, maybe it's Air Canada. They have a ton of partners, they can be transferred from anywhere. And you just start to get comfortable with how this works. You can go to the Air Canada site, you can log in, you can search. Now make sure you are on the aeroplan site, which is their rewards program. We actually got a question where someone said, how are you finding all these things with Air Canada? And you have to go to the aeroplan site, which is where you can search for all of their partner availability on different airlines. And you could say, oh, here's how this works. So just understand how that works before you kind of go too far down this path. But I think where you're going to want to go to get the most value here is on award search tools. And so I went deep on this in episode 166. If you want a breakdown there with screen sharing, go there. But I think the two starting tools that I often recommend people look at are award tool and points. Yeah, they let you search multiple airports, multiple date ranges, different cabins, different programs. They do have free tiers and paid tiers. They unlock a lot more with the paid tiers, but I don't think you need both of them. I don't think you need multiple award search tools. So if there's one that you kind of really feel good about, that's fine. I don't think any tool finds absolutely everything. And so that's a little frustrating if you're looking for something and not seeing it. But I would start with one tool. One of those two, I think is a great starting point because they have baked in flexibility. I've talked about point me in the past and I think it's more comprehensive. It's better for step by step booking instructions, but. But it's not perfect because it doesn't have really flexible searching on dates or even cities. I know that's changing a little bit and they're trying to add those features, but the last time I played around with it, it wasn't nearly as flexible as other tools or if you're really technical, seats. Aero is another kind of power user tool that has a higher learning curve but is a lot more capable. And I say that because they do a lot of caching. So we got a question about why do some of these sites show live results and some show cached results? And the real answer is that live searches take a lot of time. If you do a search on point me it sometimes takes two minutes to pull all of those results. And in the background they're running searches, sometimes in kind of browsers on servers. And it's not just like they know the flights everywhere and they've gotta go do that. And they've gotta do it differently than a Google flights would because they're having to interface oftentimes with every single program to do those searches. And that's why they don't offer so many different date options and airport options because they have really wide coverage of how many programs they're searching. Now, what a lot of these discovery tools do and what Seats Arrow was kind of one of the first people to do was that they pre run millions of searches every day or every week. And anytime a user runs a search, they store those results. And you can very quickly scan all of that data really fast because they've already searched it, but some of it might be hours or days old. And so if you're really flexible, that can be valuable. If you just want to get a sense of what's available, that could be valuable. I like that. If you want to just understand things. But if you're trying to book a real trip, you want to be doing a live search. And so most of the tools will show when that data is refreshed. And if you're doing a specific search that's narrow enough, almost all the tools are going to be focused on live data. On award tool and points. Yeah, there's kind of two sections. And then on seats Arrow they'll put up a thing that says like, your search was too broad. We only looked at cashed results. So you start to go in and say, okay, I'm trying to go from San Francisco or Los Angeles to Tokyo or Osaka, and I'm willing to go over these 10 dates in business or first class. And you can run that search. And sometimes you will find exactly what you want. And that's awesome. Congratulations. It doesn't always happen like that. Sometimes you won't, or sometimes you'll find something that is pretty good. Maybe it's premium economy and you want a business. Maybe it's flying through Seattle when you want to direct, but you can book that. And if you book it in a program that has flexible cancellation, you can kind of lock in that flight. And then what you can do is go set alerts. Alternatively, if you don't find something that you want at all, you can also go set alerts. And all of the tools I talked about, Seatside arrow points. Yeah. And award tool, they all have their own alerting services. And they are fantastic because the way they work is you set the exact parameters of what you're looking for, and when that availability pops up, they send you a message. Now, depending on how popular that route is, you might have seconds or minutes or hours or even days to go book those routes. I would be ready when you get those alerts to jump on and book things and set them for things you know you would want. But. But another option, and when it comes to learning is, let's say you're thinking of going to Europe next summer. Well, you could set some alerts for this summer just so you start to see how often are you finding things out. So this is one thing I did for Japan was I started searching and setting alerts for flights way before I wanted to book the flights. But then I also set them last year just so I kind of see how the inventory is changing, just to kind of get a sense of how it works. So no tools best for this. Like, all the tools have some alerts. I've. Because I've paid for subscriptions to multiple of them, set up alerts for the same routes on multiple tools. And sometimes one tool's faster, sometimes the other tool is faster. It's really tough to kind of know which tool is best, but usually all of them found the inventory and it was a matter of minutes between the two. And as for when to stop alerts, we got a message from a listener who said, you know, they booked flights and they got them down to 8,000 miles on American after monitoring alerts. Is it even worth setting alerts for the rest? And I was thinking, Gosh, we had 8,000 miles to get to the Caribbean or Mexico. I feel like it's probably not worth setting alerts for the sake of saving points. Because, by the way, that's another option is you might find a great flight that works, but it's 120,000 points. You could set an alert on that same route. And I've had situations where that flight dropped price and you could just change from the same program, same flight, to a lower price and get some miles refunded. In this case, I would say there's probably not a likelihood you're going to get a better deal than 8,000 points. But if there were a route that you would prefer or a time of day that you would prefer, or another day you would prefer, even if that price might not be beaten, there are reasons to set alerts on other parameters as well. And so I basically am setting alerts and keeping them active for any situation until I have the perfect flights. And so for our Japan situation, we found the perfect flights where we have all four of us flying direct in business class from San Francisco. There's not really anything else I would want to do except that there is also a first class. So I did set alerts on whether two seats open up in first class and if they did, then maybe I'd change two of our seats to first class. You know, obviously if four seats opened up, I would change all four of them, but that seems very unlikely. So that's an example of something that you might want to do. Even if you thought you found the perfect flight. It could be the time of day or something like that. But what happens when it just doesn't work? And so Sam wrote in looking for a flight from New York to Bangalore for four people in business class. And he said the best deal he found was like 1.2 million miles. There was another option that was like 1.3 million miles. It just seemed like there was nothing there. And that sucks. I've been there and the reality is that is just often the case at a single point in time. But I would be shocked if over a three month period something didn't open up. Now that might be stressful for people to think, gosh, what do I do if the flight doesn't open up? And that's where I can say, look, if it's a trip that you have to take, well, maybe you have to book it another class. If it's a trip that you don't have to take, maybe you could just wait and be flexible. Or maybe there's three destinations and you had your heart set on Bangalore, but if you could get to Istanbul, that'd be fine. So you could book that. And if things open up, you can switch and go to Bangalore. It's really tough when you see something you want so expensive and you feel like you're kind of paralyzed because it's not possible to get where you want to go. And that's why I would just encourage you to start planning further in advance if possible. But really I would encourage you to be setting these alerts because it's so tough to find what you want on the exact day you're searching. But it might pop up the next week. And so when we went to Europe for the Olympics, there were no flights when we started looking. And then three weeks later, stuff popped up and I would have never known to search three weeks later were it not for those alerts. But also I went ahead and looked into the actual flights that Sam was looking for. And, and I couldn't find anything from New York to Bangalore, but I could find stuff for 110,000 aeroplane miles to Delhi or Mumbai. And so if you think about, okay, well, the flights internal to India, there are a ton of carriers that fly from Delhi and Mumbai to Bangalore. What if you just book New York to Delhi or Mumbai at 110,000 airplane miles? Maybe that separate flight that's really short could be a 30, 50, $80 domestic flight in coach. And so that's kind of the something that I'm often doing. It's what we talked about earlier when it came to smaller airports, but even other airports. And so I did that search, found those things. So that's something I would encourage you to do. So on that checklist, it's kind of think about all the places you could want to fly to and maybe expand where you're searching and you might end up finding something that's a way, way better deal. If you have four people, this sounds a little crazy sometimes, but book two if you find them and then keep searching for the other two. Sometimes airlines only hold open two seats on a certain route. Sometimes they release two at a time, and sometimes you might not find it and you might have to pay for two cash tickets. But if you got two tickets with points for a much better deal, maybe that's worth the trade off. Or maybe one person in the family really wants to get a lot of points towards status, wants to pay their ticket, the other person can book points on miles. So if you gotta pick who is gonna fly on the points ticket versus the cash ticket, keep that in mind as well.
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every day and the reason it works
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for me is so simple. I find talking is so much faster than typing. Not because my fingers are slow, it's that typing makes me feel the need to edit.
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As I go.
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- [31:34]
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And when it comes to booking, there's one thing I didn't mention which is I'm always searching for one way flights and I'll book one way and then the next way instead of booking a roundtrip. Now if you were booking with cash, there are a lot of times where booking roundtrip with cash will give you a better deal and a better fare. And so if I were booking in a travel portal using my points but where I'm really just converting my points to pay for a cash ticket, I would look for a round trip but with points and miles. There are only a couple of reasons why a round trip could be a slightly better deal. One is I don't even know which program this is, but there might be a program out there where they would price A one way flight at the same price as a round trip flight. So obviously in that case booking roundtrip would be better. And then sometimes there are cancellation policies that apply to the entire itinerary. And, and so if you booked two one ways and canceled it, you might have to pay two cancellation fees instead of one. So that's another thing to keep in mind. Other than that I would almost always be booking one ways. It's the only way I'm searching for things now. I've talked a lot about international flights. I've mentioned business class a lot. There is a ton of value to be had there, but we've got a ton of questions. Nidhi asked a question about domestic travel and how to use points and miles for that. I get a lot of emails about this topic and, and points and miles are not just for international business class. In fact, I would argue that some of the best deals I've ever gotten are on domestic flights. They just don't often feel as great because the experience is usually saving money not getting to fly something that you would never otherwise fly. Right. The experience of knowing that I saved 40% or 75% on, you know, a United coach ticket to get from San Francisco to L. A just doesn't feel as exciting and as using my points to fly business class to Dubai. But that doesn't mean there's not real value there. The other reason that domestic flights are a little tricky is that availability is a little bit of a black box. Delta is notoriously stingy about releasing their domestic seats to partners. United's generally better and American is actually really great. But it's pretty dynamic and unpredictable about when you're going to get a good deal, when you're not. Nitty wrote in and said that she's never finding these Delta flights on Virgin Atlantic or Flying Blue, you know, and that's true. It is very hard to find them. And so it's hard to rely on these great deals. By transferring to international programs and booking domestic flights, I'd say it's a little easier. I've had a lot more luck using Aeroplan and Life Miles to book United flights. And I've had a lot more luck using Alaska Airlines and sometimes British Airways to book American Airlines flights. And so it's not impossible. But the value is often less about transferring to a program that has a better chart for getting better deals on domestic flights and it's more about finding flights where maybe one way or last minute it's really, really expensive or for some reason maybe it's a holiday. It's really expensive, but for reasons I can't explain, it can be a lot cheaper using points. And so I've often found that sometimes I'll look for short flights like San Francisco to LA and it's $300 and I can find ways to do it for 10,000 or less points. And sometimes Avianca LifeMiles is actually the best program to do that. So that's really cool. For domestic flights, there is one award tool that I didn't mention earlier that is got to be my favorite, which is the Points Path browser extension. It just sits on top of Google flights and it shows the point prices so you can quickly compare between cash and points. And it works with not every program, not as many programs as other tools, but it works with almost all if not all of the domestic programs, which makes it really valuable for domestic flight searching. So I love that. One thing that's tricky about domestic flights is that if you want to book a flight through American or Delta or United, they aren't as often transfer partners. So yes, Delta can be transferred from Amex but nowhere else. Yes, American can come from Citi but nowhere else. And United can come from Chase or Built, but nowhere else. Alaska can come from Built but nowhere else. And so yes, it's a little harder to get points in those programs. And yes, a lot of the domestic carriers don't release as much inventory so to their foreign partners as you'd want. And so I guess my answer, which is not the perfect answer here is don't stop looking but maybe think about diversifying points. If you know that you have points in Amex and Chase, that gives you United and Delta, if you have city points or built points, you can get to Alaska or American. And so that is one reason that I like to have a handful of miles and in different programs and it's for domestic flight booking because I find that on a lot of international flights you'll find partner availability easier because a lot of those flights are on those partners. But domestic it can be helpful to have a few points in different places, which is actually easier to do for domestic flights because you don't need a few hundred thousand points for a long haul international business flight, you might only need 20 or 30,000 points for a trip in short haul economy, which means that you can have kind of enough points in two or three programs for domestic travel from just a couple of card bonuses across two or three programs. And another question we got from Taylor was is it ever a good deal to use your Points to upgrade your seats. And every place I look, every person I asked, the answer was no. There are a lot of great ways to upgrade flights with different instruments that are not your points. So United has plus points, there's global upgrade certificates, all kinds of stuff like that. But when you use your points to upgrade, it's not something that I've often seen a good deal except for maybe a few rare cases. I know there were used to be decent at the gate with Emirates to upgrade with points, but that upgrade inventory is pretty limited and often doesn't clear until the day of and often you don't get priority you using those points to upgrade as someone you know using your points versus having status. And so my advice is if you're really trying to get an upgrade, you're better off just booking the flight in that class. Now the reason Taylor asked this question was because her work often will pay for economy and will not cover her business class travel. But she wants to use her points and close that gap. And so I will leave it to anyone listening to decide how this might make sense for them and their work. But some options that I've used in the past one, you know, you could ask your work if you could book business class pay for it and you cover the difference between an economy ticket and many work travel programs might pay for full fare economy. So it might be closer than you think. Not all of them do, of course. You could ask your work if you could book your business class flight with miles, but you could submit an expense for the paid ticket for economy, which could be a great option. Sometimes you could probably book that flight in economy and cancel it for a credit that you could use some other day and then book the business class flight directly with points. So there are a few options like that that could work. Or if you focus on earning status from your credit card spend and whatnot, maybe you can earn some of those instruments that make it easier to upgrade those flights. None of those are perfect. Like in a perfect world, you could book an economy ticket and just use your miles to upgrade to the business class ticket for a great deal. And it just unfortunately doesn't often work like that. And I know very few people who've ever told a story about using your miles to upgrade being a great deal. That's kind of how I think about the process of looking for being flexible and booking award flights. So we just talked a lot about transferring points and miles to airlines and other programs and I want to come back and talk about the portal because I used to Say never transfer in the portal. The only way to get great value is by transferring to airlines and hotel groups and booking. There's. And I think the only way to get really crazy outsized value is to do that. You're not going to get 5 cents in the portal. But as I've kind of broken down a few things, I'll highlight them and reference you to go deeper. I think that there is a case for the travel portal for some programs that is probably better than I originally gave it credit for. And so I'll start with a case against it and why so many people don't like travel portals. And I put myself in this camp and that is that for many programs, changes and cancellations are really painful because you get referred to the place you booked the flight. You booked a United flight through bank of America's travel portal, which I have done. I reach out to United, we had to cancel the flight, contact bank of America. Okay, so we cancel the flight, I have to rebook the flight, contact bank of America. It's just a pain. It just makes everything harder. For hotel bookings, this is not always the case with kind of luxury bookings, you know, the edit fine hotels and resorts. But in a lot of the kind of base tier hotels, even if they're Hilton or Hyatt hotels, you don't earn points on those rooms. You probably don't get your upgrades if you have status, all the other elite benefits might not be there. And so you kind of get treated as a second class citizen if you book your hotel through a generic portal. Now the luxury programs that a lot of these portals have added oftentimes don't have that same experience, which is great. And then in some portals they even make it clear this is a direct booking that you're going to earn points on at Hyatt and this is not. So that's something to consider. And then flexibility can be really limited. Putting together some creative routings, the way you search isn't always as straightforward with the portals as it is on the airline websites because there just aren't as many options. I tried to book a refundable fare once on the US bank portal because I had a credit to use and, and I couldn't figure it out. Like there was not a way to book a refundable fair or one time I wanted to book a round trip ticket where one leg was in business and one was in coach and it wasn't possible. And so that is another reason not to love the portal. And then another one is sometimes the Prices in the portal are just not as competitive as even cash bookings outside of the portal. Sometimes they're better. And so I saw this big audit of all of the different portals and how do the prices compare? And there was basically no consistent answer. It wasn't one portal was always better than direct with the hotel. Sometimes better, many times worse. Sometimes one was better and then worse for the next search. And so you've got to make sure you at least do a little bit of a comparison. The last thing that I hate about the portal recently is that it's gotten to be a less good deal. Chase used to say all your points are worth one and a half cents if you have a sapphire reserve card. And now they've said, well, we're going to let you keep all the old points at that rate for some period of time, but going forward it's going to be very dynamic. But we have this awesome points boost program that since they've launched, seems like it's less valuable. And so that's the case against the portal. But the case for the portal is that it's so easy. You don't need to go find a word availability. Every flight that you can buy with cash is there. It takes a lot of stress out of booking things. The integrations have gotten better. So Bilt now has a direct booking integration with United, where you can book United or some hotels and get treated as if you booked a flight through United. In fact, if you're booking United flights, I think booking them on Bilt is better than booking them on United because you get treated like you booked them on United, but you get one built point per dollar for that flight on top of that. And so as portals can evolve to do a lot of these direct bookings, they get way more interesting in my mind, if I don't have to deal with a portal customer service, if I still get treated like I got my status, I got all of those things, I'm going to be booking the portal all the time. And so the build portal is a little bit interesting for, for certain airlines and hotels versus other ones. So it's super easy. It's getting better. When you book premium properties, there are a lot of travel incentives. So almost every premium credit card now seems to have a 200, 300 off, $100 credit for booking in the portals. So if you're looking at a hotel room, that's $500 a night and you could book it with points or you could book it in a portal where you have a $300 off coupon and makes it $200, it's probably going to be a better deal. And so as those coupon books stack up, not to say that you should keep a credit card, because these coupons exist necessarily, that's a separate conversation. But if you already have them, the portal can often be great because you might be getting 40, 50, 60, 70% off through some of the perks that come with your cards. And that's another compelling reason to use it. The other big one that has really changed my thinking is when I went deep on in episode 258, which is that when you book in the portal, you're booking a cash rate. And what that means is that in most airlines and hotel programs, you're earning a lot more points for your flight and your hotel because you're paying cash. You're also earning points by booking it in the portal. And this is true whether you're redeeming points or not in many cases. So you're earning points from the portal, you're earning status, you're earning points from the airline. That kind of effective value could be really, really high. There are cases where I've compared booking with points to booking with cash, including booking in the portal and the effective savings booking in the portal. Because of the points, the status, the credit card points you earn for the purchase, the portal bonuses can be worth 10 to 25% off that flight. In some hotel situations, you might earn 20 something hotel points per dollar spent on the hotel, whereas you might earn nothing if you book it with points. And even though many hotel points, especially the ones where you're earning 20 something points per dollar, are worth way less than an airline mile, they're not worth nothing. And so that is something to keep in mind. If you think about how much value am I getting for my points? You need to make sure you factor in the fact that when you book with cash, you're often earning a lot more from the portal, from the hotel booking, from the flight, from your credit cards than you would with points. That said, there are still tons of opportunities to beat that 10 to 20% discount, but it's just something that needs to be compared. Now, quickly coming back to points boost, since I know there are a lot of people listening with Chase points, and it's a question specifically that Woody brought up, which is like, how do I think about points boost and how does that work? And it's a lot more nuanced than I want it to be. They've kind of changed the points boost program from you're guaranteed to get $0.02 per point on certain hotels in the edit collection to you might get up to 2 cents a point. And so I think NerdWallet went and looked at over 10,000 flights. They found that about 9 1/2% of them qualified for any points boost. United was the most consistent. And so you know, if you're booking United flights, you might be able to get over one and a half cents of value from points boost features. But if you're booking other airlines, you might not. And so when I think about the travel portal, if you're able to get one and a half, two cents of value, that's way more exciting to me than if you're only able to get one center for $0.01. There are often ways that you might even be able to cash out your points and then book directly with the airline for that same value. I would want to make sure if I'm using the portal I'm getting more value than I could get cashing out, of course. But I also want to get some value to make up for all of the other challenges that come with it. And the only other thing that's hard to compare is flexibility. A lot of cash bookings in the portal. Whether you're paying with points or paying with cash, the flexibility to cancel is not as simple as sometimes it is when you book with points points, whether that's a hotel or an airline. So I think if you're really flexible, you're probably still going to win with transfers. But it's not impossible to get enough value that it makes it worth playing the points game just booking your flights or your hotels in the portal.
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- [48:30]
A
So up until now we've talked mostly about flights. I want to cover hotels briefly because one, we got a lot of questions about it and two it's just a different beast. And the primary reason is that there aren't that many hotel programs that you can transfer your transferable points to and most of them are not worth doing that transfer. Maybe sometimes with a transfer bonus. But the reason is that a lot of the transfer rates just don't make it worth transferring points because you actually could get more value in the travel portal. So Marriott points are often worth somewhere around.07 cents. Hilton and IHG in the.05.06 cents. So less than one cent a point. So if you're looking at your points and you can transfer one chase point to one Marriott point to get 0.7 cents a point, or you can just use your Chase points in the Chase travel portal to get one to one and a half cents a point for Marriott, it's going to be a way better deal. So if you want to use your points to book hotels because you don't want to spend the cash, oftentimes with most hotel programs, you'd be better off either booking in the Chase portal or cashing those points out in some way, depending on the program, it might be a saving credit, it might just be a cash out, it might be transferring them to your brokerage account and then using that money to go and buy points or book the hotel. And so that's why I think as much as I really like hotel programs, I really like having points and booking them, getting them from, transferring from transferable point programs is often not a great deal. Hyatt's the clear exception because Hyatt points and the way their program works, they're just more valuable, not more valuable in the sense that earning Hyatt points is more valuable than earning Marriott points, but one Hyatt point is more valuable than one Marriott point most times. And the transfer ratio from Chase is one to one for both of them. And so that's why I think that Hyatt is a better program for transferable points because the individual value from a point is worth more. Now, if Chase said transfers to Marriott were 1 to 3, I transfer to Marriott all the time, that'd be a great deal. I've also talked in the past, you know, I think it was episode 2:44, about buying Hilton points. And so if you can cash out your points to cash and buy Hilton points, if you don't have them, that's probably going to be a better deal than transferring to Hilton points because the transfer ratios to hotel programs just aren't as good as sometimes just buying them directly from the program. So then that asked the question that Katja wrote in, which was like, how do you get hotel points? If you really wanted to book a hotel like the St. Regis and Bora Bora and you needed Marriott points and you only have Chase or Amex or some points that transfer terribly, how do you actually get those points? And the short answer is that if you want to earn a lot of hotel points, it's probably going to be from staying in hotels or from those hotel program credit cards. And sometimes they're really lucrative. Right now the Bonvoy Brilliant card is a 200,000 point welcome bonus. After spending $6,000 in six months. You can regularly find Hilton welcome bonuses in the 100 to 175,000 points. Sometimes even with a free night, which is happening right now, other Marriott Bonvoy cards are doing up to four or five free night awards. So there are a ton of ways to get free nights and, and hotel points from credit cards, just not from transferring from programs. Caveat other than Hyatt. And so the way I've accumulated most of my hotel points is from hotel credit cards, hotel credit card welcome bonuses and from a time when traveling for work was paying for hotels and I was paying for them with my hotel credit cards. I would say you've got to look around at different hotel cards. And by the way, if you want to find whatever the best hotel offers are now, you can always go to all thehacks.com cards. We have links to all the cards that are out there and all their welcome offers. And we do our best to send you the best deal, whether it's a deal that supports the show, whether it's a deal that's a referral link from a listener, or whether it's just a link straight to the website of the issuer. My goal is to put the best offers there so you can have one central place to find them all. A quick redirect was in that question. Katja was trying to find trip to French Polynesia to go to Bora Bora and looking at the St. Regis and I would say if you don't have points on merit, maybe you could consider the Conrad and Bora Bora. I happen to have been to both. They're both excellent. Hilton often makes it really easy to buy points and so you might be able to get that Hilton stay for a lot less. And one Hilton credit card can get you diamond status, which would get you a lot of the same treatment that you would get staying at a Marriott property if you already have status there. And so it can feel like, gosh, I've earned this status on this one hotel group. I want to stay at a hotel in this program. But maybe you can get a 2,3x better deal at another program where one credit card could cover the stay or at least a few nights of the stay and get you the status you need to be treated just as well. So it seems a little crazy when you go all in on status, which is why I might consider not going all in on status, which is another one of my big mistakes, I think. But I just can't help myself sometimes. But I think that's kind of how I think about it. For a lot of boutique hotels, they're just not an option. And I actually think that's a little relieving. That's where, you know you can use the portals. You probably have the highest chance of the Chase Travel Portal boost being worth 2 cents. And so that's where you're probably going to get a lot of opportunities to use your AMEX Platinum hotel credits and whatnot. So let's come back full circle to Matt's question, which was what do we put on a 3 by 5 index card? Like I said, I think you might need small handwriting for what I'll say, but you probably don't need microfilm. So I'd say, you know, side one of the card, I would put the process and I would say, you know, one, define your flexibility. Even one dimension of flexibility will unlock your deals. Two, think about region to region. So don't necessarily search San Francisco to Santorini, maybe search west coast to Europe. Three, start with one tool, but if you're proficient, maybe search with a few tools because there's not one tool that finds everything. But don't start there. Start getting used to one thing before you try to do everything. Number four, book something good and set alerts to find something better. Five, book one ways but make sure you understand all the cancellation policies. Six, don't transfer points until you're ready to book. So that's kind of the process side. Maybe on the other side of the index card we could put some mindset shifts which are that one points aren't always worth what you think. Factor in all those other factors of earning status, earning points, earning credit card points, earning portal bonuses. That comparison matters. Portals aren't as evil as we might think, especially sometimes the earning on them. You know, earning 8 to 10x booking in the portal can be really interesting also. Especially if someone mentioned they're booking for work and they've got to pay a cash price because they need a receipt. They know they're going on the trip. Portals have a place. They might not have a place for the very flexible person who wants the best deal, but for someone who has a lot of points and they just want to take a free vacation, it can be a great option. On hotels if you're trying to transfer your points, it's really a high game if you have chase or built points. If you have other point programs, you know it's going to be a lot tougher to get outsize value with hotel points. So I would say probably focus on airlines or book hotels in the portal. I think another big mindset shift is just getting comfortable with the concept of good enough. Because things change all the time. And so the more you do this, the more you understand that, the more you feel good about it. And I think that's probably the number one mindset shift that has made this successful for me and that the more I share that process with my wife Amy, the more she gets comfortable with it is we can commit to going to a place before we have the flights and we can be comfortable booking something that we probably don't love taking, but it gives us the kind of satisfaction of, okay, well we're definitely going. Cause we have some flights and we can change them as things evolve. And getting comfortable with that uncertainty is probably one of the biggest mindsets you can have to be successful with award booking. And then this is one that I don't even know why I'm the one giving it because I certainly don't take this advice regularly. But don't necessarily hoard your points forever. They devalue over time. Cash grows, points don't. So use them right. Like don't be afraid to use a portal booking if it gets you on the trip and uses the points, especially if you're regularly earning more and more of them. I think it's something I need to work on. It's something that I know a lot of people don't love as optimizers because they know they could do better. But also it feels really good to just go on a trip for free. So that's my parting advice. I hope this is helpful to run through a bunch of your questions, but also kind of just try to put it in a little bit of a narrative. Thank you to everyone who sent in questions on Booking Travel with points. This year we're going to tackle questions more regularly, so please keep them coming. You can share them@AllTheHacks.com AMA for Ask Me anything or you can just send an email to podcast allthehacks.com that is it for this week. I will see you next week.
- [57:29]
C
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