Traveling for free isn't just about earning points, it's about using them smartly. But if you've ever searched for a ward space and come up empty, burned more points than you should have, or run into other roadblocks getting the most out of your points and miles, don't worry, you're not alone.

It's something we all face. So today I'm going to share 18 of my favorite tricks for actually redeeming those points for flights and hotels, including how to find the best deals, navigate airline rules, and make sure you're never stuck paying more than you should. I'm Chris Hutchins. If you enjoyed this episode, please share it with a friend or leave a comment or review.

And if you want to keep upgrading your life, money, and travel, click follow or subscribe. I am really excited to help you all use your points and miles to book some incredible travel. And if you're not familiar or you haven't been listening for a while, I just want to remind everyone that sometimes the best way to get outsized value from your points and miles is to transfer those points and miles to airlines or hotel groups, or maybe you already have points and miles sitting in an airline or a hotel program from flying or staying with them.

And so today's episode is really about figuring out how to use those airline points and miles, whether you've earned them in that program or transfer them from a credit card so that you can get the most out of it. Oh, and for anyone not familiar, when I say award redemptions or award travel, that just means travel booked with those points and miles.

Okay, so and here's how we're going to break the episode down. I'm going to start with the foundational strategies that make or break most award redemptions. These are things like flexibility, booking windows, search tools, and how to understand program rules. From there, we'll dive into all the tactics for finding and booking, including sweet spots, hidden availability, stopovers, leveraging positioning flights, and more.

Then I'll get into a few things that I know trip people up like fees, travel coverage, and married segment logic. Finally, we'll wrap with some hotel specific advice and a few niche but very helpful tricks for families and Southwest travelers. So whether you're booking your very first award trip or you've been doing this a while and you just want to keep leveling up your strategy, I promise there is something in this episode that's going to help you travel better, use fewer points and miles than you expected, and enjoy your next vacation even more.

So let's start with flexibility, which is the first thing I want to talk about because the most successful award travelers tend to be flexible on some aspect of their trip. But I think sometimes people get caught up on what flexibility means and they think, "Oh, flexibility, it's just about being able to fly on any date and I can't do that because I only have specific dates off work." Well, that's not true.

When I say flexibility and that flexibility unlocks so much, that could be flexibility with your dates for sure. If you could go to Europe and you can go anytime, that's going to make it even easier to find a great deal. But it also could be flexibility around where you go.

So you might say, "I have very specific dates but I'm willing to go anywhere." It might be flexibility on what airlines you fly on. I meet some people who say, "I really only want to fly Delta." Well, that's going to make it really tricky. But if you're flexible on, well, I don't care where I go.

Or I don't care if I have to change planes a few times. Or if I route a different way, like from California down to Florida to get to Europe. That might not be the most direct path there, but it might be the path that has the best deal. And at certain points of your journey in this points and miles game, that might be what you're optimizing for.

It might be flexibility on which cabin you're in. If you're just trying to redeem first class or business class, that could be a little harder. Not impossible by any stretch, right? I've done it hundreds of times. But if you're flying economy or premium economy, that might make things even easier.

And then another one that I think a lot of people don't always think about is the flexibility around when you can lock in the trip. I know a lot of people who say, "Well, I want to go to Europe and I want to go this week. And in fact, I really want to go to Paris." And I say, "Well, the one piece of flexibility it sounds like maybe you could have is when you book the trip." Because if you wait till the last minute, you might get a really amazing deal.

Or if you can plan it over a year in advance, you might get the best deal. So deciding when you're going to be able to book that trip is another form of flexibility. Because the average traveler is looking to book a trip somewhere around, I think, three to four months out.

So if you can deviate from that and book it a year out, or if you're comfortable waiting until two weeks out, things open up so drastically in that last two-week window that I would argue that that's kind of the best time to buy. But I'm going to share a few tactics to make that less stressful because I know very well, I've had many conversations with my wife, the idea of waiting until a few days before we leave to know that the trip is even happening can be really stressful.

So there are ways to avoid that. And we're going to talk about them. One other thing, actually, that we are using for a trip to Japan next year is we didn't have flexibility on dates. We didn't have flexibility on when we wanted to go. And honestly, with two young kids, we didn't want to be flexible about the weather we changed stops.

We wanted to go direct. And honestly, we wanted to go direct on a flight in business class. So where we were flexible is we were able to find flights, one from San Francisco to Haneda and one from San Francisco to Narita, the two different Tokyo airports. And so my wife and I, at least right now, and we'll talk about what might change over the next coming months.

But we split up and each of us is on one of those flights with one of our children. And so that is another form of flexibility. So I think you've got to decide where you can be flexible. And the more flexible you are, the easier it's going to be to find amazing deals.

But even if you're not flexible, I think you can still find great deals. And we're going to walk through a lot of ways that we're going to make that happen. The next thing I want you to understand is that almost every airline has a handful of different airline partners.

Now, sometimes those are part of the big three airline alliances, SkyTeam, One World and Star Alliance. And sometimes they're just one-off partnerships. Like Alaska has a one-off partnership with Condor, which gives you access to a bunch of flights to Europe from the US, even though Condor is not part of the One World Alliance.

And every single one of those partners has a different award price, a different fee structure, and a different way things operate. So just to point an example out, I'm going to look at this one flight right now. It's a flight from Boston to Amsterdam on Delta. And the retail price of that flight right now is $2,700.

And you can book it with Delta miles. It's 240,000 Delta miles plus $6 in taxes and fees. Now, that's a lot of points. Maybe that's a better deal than spending $2,700 if you really want to be on this flight. But if you look at the other options, and I'm using a tool called point.me, but we're going to talk about some other tools today, you can actually book that flight for as low as 47,500 points using Virgin Atlantic Flying Club.

And at first glance, you might say, well, that sounds like a great deal. That's way less than 240,000 points. But Virgin Atlantic is one of the airlines that, depending on the route, can have really high fees. And so the fees on this flight are $1,054. I think I'd still rather pay 47,500 points plus 1,054 than 240,000 Delta points.

And it's even better if you have chase points, because right now there's a 25% transfer bonus. So you'd actually only need 38,000 chase points to be able to have 47,500 Virgin points. But neither of those are as exciting as the fact that Flying Blue, which is the frequent flyer program of KLM and Air France, you could book the same flight for 64,500 points and only $33 in taxes and fees.

So let's ignore the Virgin Atlantic option now because such high fees and say, Delta, 240,000 points, $6. Flying Blue, 64,500 points, $33. Way better deal. Now, you could also book it through Korean Air for 80,000 points. But I'm going to guess most of you you don't have Korean Air miles because it's very difficult to obtain them if you're not flying on Korean Air because they're not a transfer partner of anyone.

So that's just an example of how it can be much, much cheaper to go look at other programs. And if you were stuck in the mindset of I'm flying on Delta, I should book through Delta, you might completely miss the fact that there are so many great ways to book it.

And in this particular case, Flying Blue and Virgin Atlantic are partners of Chase, Amex, Built, Capital One, Citi, and Wells Fargo. Basically, if you have transferable points, you can get them to Air France and Virgin Atlantic and get a way better deal than what you'd get booking with Delta.

Just to paint another example, you can often book American Airlines flights with British Airways, Avios, which can be a great deal for short domestic flights. But on long haul flights, Avios similar to Virgin Atlantic often has high taxes and fees. So you'll always want to make sure you're looking at lots of different airline partners, but we're going to talk about tools that make that so easy that you almost don't have to think about it.

The next is that you want to understand the different rules of those programs. So yes, sometimes they take different miles, sometimes they have different taxes and fees, but often they have different cancellation policies. Now, depending on how certain you are about this travel and how far out it is, might change how important these policies are.

But there's a few airlines that I want to highlight, like Iberia, which might sound like they have a good deal when you see it, but Iberia awards on partner airlines are non-refundable. Meaning if you don't take that flight, you cannot get your points back. So I would strongly advise you, unless you're looking at a flight that leaves in three or four hours and you're at the airport to not book partner flights through Iberia.

Etihad is similar, except they keep somewhere between 25 and 75% of the points, depending on how far out you cancel it. But still, that's a massive, massive penalty. Whereas there are lots of airlines, most of the domestic U.S. ones have no fees. Alaska has a $12.50 fee for partner awards.

I know that there are a handful of European airlines where the fee might be $25 to $50 to $70 to cancel. So in my mind, if I'm planning a really big family international trip that I'm pretty confident I'm going to take, but the penalty is $25 or $50 if I have to cancel it and I get all my points and miles back, that's okay.

But if it's more speculative where I'm not even sure if I'm going to take it, sometimes I might pay a few more miles to be able to book it from a program where I can refund it with no penalty and no cost at all. So that's kind of how I'm thinking about this.

A couple of cool, interesting hacks here. So LifeMiles, which is the program of Avianca, they actually have high penalties for canceling flights that you booked with points, but they have this program called LifeMiles Plus. And I think it's somewhere between $20 and $40 a month and you have to commit for six months.

Though when you commit, you get this kind of monthly deposit of miles, but it completely waives all your award fees. So if you were to book something and you needed to cancel it and you didn't want to have to pay those fees, it might be cheaper to join LifeMiles Plus and get all those fees waived.

Also United has this ridiculously amazing thing where even if you book a flight with points and you forget to cancel it and you miss the flight, they will even redeposit the miles on a flight that you forgot to cancel before it took off for only $125 fee. Now, most airlines, I think you're completely forfeiting your miles if you don't cancel it before departure.

In fact, British Airways one time, I didn't realize they require you to cancel 24 hours out. And I didn't know that. And I saw a flight that I thought was slightly better. So I booked a different flight than my British Airways flight, forgot to cancel it, and lost $62,000.

just because I forgot. And that was a painful lesson, but it's just part of the process. So that's cancellation policies. The other really important thing to understand are expiration policies. So many airlines, as long as you have some activity in your account, will keep your miles active. And that activity doesn't always have to be flying with the airline.

It could be transferring in a thousand points from, you know, one of your credit card programs. Many airlines, as long as you have some activity in your account, will keep your miles active. And that activity doesn't always have to be flying with the airline. It could be transferring in a thousand points from, you know, one of your credit card programs.

It could be buying a magazine subscription. It could be donating some miles. For example, American Airlines is notorious for canceling your miles after two years if you haven't had any activity. But if you do anything with those points and miles, if you open up a Basque Bank mileage checking account, leave a small amount of money in where it deposits, you know, your interest in the form of miles each month, your miles will never expire.

Also, sometimes airlines have shopping portals, make a purchase through the shopping portal, credit the miles, miles extended. However, there are some programs, notably ANA and Japan Airlines, that have hard expirations, and there's not a way to avoid them. There is a way if you want to go earn millions of miles with Japan Airlines and get into a status that removes their expiration.

But for almost anyone listening that isn't so far down the Japan Airlines rabbit hole that they already knew that, those programs you can't extend after, you know, those miles arrive. And so those are programs where I'd be very, very cautious transferring to unless you were really sure you had a booking to make or you really had a lot of flexibility in the next few years to use those points and miles again.

So know the program rules before you transfer. It's really easy to go search online award expiration policies by airline, and there's some great posts on different frequent flyer blogs that you can find. I'll link to a couple of them in the show notes. This episode is brought to you by Masterclass.

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And I'll link to a great guide that Devin Gimbel, who came on the podcast a few weeks ago from Point Me to First Class, has that you can download of when all of the different airlines open their schedules. For example, Japan Airlines actually opens their schedule at, I think, 361 days out.

They're in the One World Alliance, but American Airlines doesn't actually open up their schedule or let you book until 331 days out. So you might think, oh, wow, Japan Airlines, I'm going to go grab one of those seats the moment the schedule is open. But if you're planning to book those seats with a partner, and that partner doesn't let you book until 331 days, you're going to have to hope those seats stay there for 30 days before you can book them.

So it's important to understand when different airlines let you book seats. And the reason it's important is because some airlines have a practice where they just specifically drop a certain number of seats every day. And Japan Airlines is one of those. You can almost always find two business class seats on Japan Airlines on every single route the day they release the schedule.

But if you're trying to book them from a program that doesn't have access to Japan Airlines or does but doesn't have access at 361 days, you'll find yourself in a situation that you can't book those flights. So on the Star Alliance side, Avianca lets you book 360 days out, Aeroplan lets you book 355 days out, but United only lets you book 337 days out.

So similar process there. On the hotel side, almost every hotel group lets you book about a year out. Hyatt goes a few months past that. I think it's 13 months around there. Accor, I think it's around 13 months. And then Radisson, somehow they let you book two years out.

So I think depending on the hotel program and the airline program, you'll want to look these up. I'll link to a guide that you can download that Devin put together and you can get all that. Some other programs have reliable windows where maybe six months out or 14 days out, they release more seats.

Lufthansa is notorious for only releasing their first class awards to partners within the 15 days before departure. And there are tools that make this really easy. So seats.aero has a bunch of tools like the Lufthansa first class finder, the Qatar Q suites finder, the Japan Airlines first class finder, where you can actually just look for those routes that are really hard to find.

And you'll see right here that Lufthansa's first class is only available in the next three days, but there are 10 routes you can take. So if you want to go from Boston to Munich in first class, you could do it. It's 140,000 points through United. And that's a way to get access to that ticket.

Now, that doesn't mean that United, again, is the only place you can book it, but that's how they're searching this inventory with this tool. And that's really my next thing that I want to talk about, which is understanding these award search tools. Now, if you go back to episode 166 and 167, I sat down with Greg from the frequent miler and we broke down all the best tools for booking flights.

And then the next episode on hotels. So I'm not going to do a masterclass on flights and hotel award search tools because I've already done that. But I'll just broadly remind everyone how these tools work. And there's really two searches you'd want to make. So one of them is a discovery search.

And for that, I think Points Yeah has this daydream explorer, which is a really cool thing where you can say, hey, take me from the United States to anywhere. And then you could say, oh, I'm looking for a beach and I'm looking for something that I can transfer my points to from Amex.

And I'd like to find it in business class. Tell me what you can find. And it'll just show you all these ideas of what's possible. So, for example, I'm looking right now. Oh, I can go to Italy for 55,000 points in premium economy. Or I can go to the Maldives, 35,000 points in economy.

This is great for when you're really, really flexible. These discovery tools that are just like, help me get the most out of my points and miles. Then on the flip side, there are flight search tools. And they can let you say either San Francisco to Tokyo. Or depending on the tool, some of them let you say San Francisco to Europe.

Or West Coast airports to Europe. The one I probably use the most is Award Tool or Seats.Aero. But almost every one of these tools has both of those features. So I'd encourage you to play around with them. Most of them give you free access to search in a limited window, like in the next 60 days.

And the paid tools give you a longer window to search. So find the tool that you get the most value out of and explore that. Another tool is Point.me. They recently also offered something like that flight discovery tool. They call it Explore. But the thing that I think they really shine at is two or three things.

One, on the search side, I feel like they have a great set of partners. They used to have at least the most number of partners. So if you found a flight you specifically want, you just want to know where's the best place to book it for the best deal.

Point.me has that data. I really feel like they have a comprehensive list. But where they really shine is that they're going to walk you through exactly how to do it. They also have a concierge where you can spend $100 to $200 per person. And they will go out and do all the searching and do everything for you and walk you through the whole process.

So having an award search tool is really important. On the hotel side, there's a ways, max my point, and stay with points that are all different ways to search and set alerts for hotels. And a lot of these tools have added hotels as well. So actually, Points.me, I think, has hotels.

Award tool has hotels. Seats.arrow launched rooms.arrow. If you're kind of a spreadsheet nerd, Seats.arrow is probably going to be your favorite tool. But definitely go back to that episode. The other tool that I'll include on this list that is a little bit different is called PointsPath. And the way that tool works is it's an extension that sits on top of Google Flights.

So if you search for a flight, it'll tell you, hey, this flight's $419 or 37,500 miles on United. Use cash. But if you scroll down, I'm looking right here, $419 on Alaska or 20,000 points, it's a great deal. Use your points. And so it layers it on top of your searches you're already doing on Google Flights.

But it has a very limited number of airlines it supports. So I think it's a really good tool for domestic because they include all the domestic carriers. But if you're looking for kind of long-haul, complicated international flights, I don't think it's going to be as helpful. The other tool I use a lot is called Flight Connections.

And the reason I use that is because you can basically search for an airport and it'll just tell you all of the flights that fly directly from that airport. So it's pretty helpful if you're thinking, oh, where can I fly direct? Who flies out of this airport? Or when we talk about positioning flights in a little bit, I'll explain how I use that tool as well.

Finally, I'm hopeful that as AI agents get better and better, they can learn to use a lot of these award search tools and help all this process. But I haven't seen that yet. The last foundational tip I want to share is around buying points. Just because you don't have the points in your account doesn't mean you can't take advantage of some of these amazing deals.

Points are very, very often on sale. And in the case where sometimes I've been able to get four, five, six cents a point, you can almost always buy points for less than four cents. You can almost always buy points for in the one to two cent range, depending on the program.

And on the hotel side, they're often down as cheap as half a cent. I know I've seen Hilton points and Choice Hotels points down at half a cent pretty regularly. So points are always on sale. Some airlines like Avianca and Air Canada are notorious for putting points on sale all the time.

So I think Avianca had their points on sale 13 times back in 2023, Air Canada 10 times, Hilton 6 times, British Airways 8 times. So I would say using these award tools to see if there's an amazing deal, even if you're not really deep in the points and miles game, is still valuable because you might be able to buy those points at a price that still makes the flight cheaper than if you paid cash.

So that's kind of some of the foundational stuff that I think you need to know. You need to be flexible, but not in the way you might think. You want to look at all the different partners, understand their rules, understand when their schedule is open, find an award tool that you can use to search, and consider the fact that you can buy points.

So if you find an amazing deal and you don't have the points, that doesn't mean you can't take advantage of it. So let's jump into the tactics. So the first one I want to talk about is finding award sweet spots. And the thing that's interesting is that every different airline has a different way that they price flights using their points and miles.

And sometimes they have one way they price flights on their own airline and then another way if you're using a partner airline. And some of those are dynamic, meaning they don't actually have an award chart. They don't tell you how much it's going to cost. You don't know until you search.

And a lot of the U.S. airlines have started adopting that program where you just search and it just tells you a price. Now, if you've done this enough, you kind of have a sense of, oh, when it's low, it's going to be about this. But when it's high, it's somewhat correlated to the flight price and it could be quite expensive.

But other airlines have either distance charts or zone-based charts. And so Air Canada, for example, on their partner airline chart, there's actually a set price depending on where you go. For some airlines, that's based on distance. So you can go up to 12,000 miles or something from a destination and it's going to be the same price.

But the reason I bring this up is because for each program, there are some really, really great sweet spots that can be awesome ways to take advantage of points and miles. So Turkish Airlines, for example, charges 7,500 miles for one way and economy within the continental U.S., but that includes Hawaii.

So if you can find space on United to Hawaii within the U.S., you can get that for only 7,500 miles. That flight on United might be 25,000 miles or more. British Airways uses a distance-based award chart. So it can be really fantastic for really, really short flights. So flights under 650 miles might be as little as 4,500, obviously, in one-way economy.

Maybe you're going from Miami to the Bahamas or Hong Kong to Taiwan. Being able to do it for that small, small number of points and miles in a scenario where that cash price might be way, way higher and the price that most U.S. programs charge might be way higher.

So you can start to learn if you search for sweet spots getting to a certain place. That can be really, really powerful to find great deals. Then on the hotel side, Hilton free night certificates have no cap. So the sweet spot with Hilton free night certificates is finding those hotels that cost the most, which in a recent devaluation, I think now it's up to 180,000 or 200,000 points a night.

And for people who are using Hilton points, that's a bummer because it might have gone up 50% in terms of the number of points you need. But if you have free night certificates, at least right now, that doesn't really matter to you. It doesn't matter if the hotel is 180,000 or 30,000.

Those free night certificates work no matter what the price is, as long as it's a standard award. Now, sometimes you'll go to Hilton and it'll say 2.8 million points for this room. Those don't work for free night certificates. That's their dynamic pricing. Definitely want to steer clear there. Next, let's talk about transfer bonuses.

I briefly mentioned earlier that, you know, if you were looking at a Virgin Atlantic flight and it was 47,000 points, transferring from Chase right now because there's a bonus makes it even more compelling. And so right now, there's 30% bonus transferring from Amex to Avios, 25% from Amex to Hilton, 25% from Citi to Wyndham.

And these are changing all the time. So don't read into anything I just shared. By the time this comes out, all of those will probably be expired. But I looked back over the last few years and every year since 2021, there's been over 50 different transfer bonuses. And in 2025, just in the first five months, there's already been 30.

So transfer bonuses are amazing. They typically range from 15% to 20% all the way up to 50%. Except in the case of built, they have these crazy transfer bonuses sometimes that have been as high as 100% to 200%. So transferring one built point into two or sometimes three miles in another program.

Pretty amazing. But the transfer bonuses are only when you transfer the points from that transferable currency to that airline or hotel group. And they're not reversible. So as much as I love the fact that there are these amazing deals, I encourage people not to necessarily jump in and take advantage of them until they're ready to book.

Unless you're really, really comfortable with that program and you know how you're going to use those points in the future. And I say that because I was really comfortable with Air France. And so I transferred in some points to book a flight that we weren't sure if we were going to take.

We ended up not taking it. And I felt really comfortable about Air France. So I felt comfortable with that deal. Well, it turns out that Air France last year, the year before, was really generous at releasing European award space in business class. This year, they have not been quite as generous.

So I have some Air France points and I don't have an easy way to use them anymore until they start, hopefully, releasing more space. So just keep in mind that those transfers are not things that you can reverse. But if you're looking to book a trip and those transfer bonuses are happening, it can just further reduce the number of points you need to have if you're starting with transferable points in Chase, Amex, Capital One, etc.

In addition to transfer bonuses, they're often award sales. So flying blue regularly, as much as they might not make wide open U.S. to Europe inventory as pervasive as it used to be. They do have these promo rewards every month. They can be 25 to 50% off. And British Airways often does off-peak pricing.

And these are things we put in the newsletter. Anytime there are new transfer bonuses, airline mileage promo rewards. So if you're not subscribed, allthehacks.com slash email if you want to stay on top of that. The next tip is to almost always book your award travel with one-way flights. There's a couple reasons for this.

One, you don't have to book roundtrip. When you book a lot of international roundtrip flights with cash, you get a much better deal than one-ways. But with miles and points, there's almost never a scenario, except for maybe one or two programs that I don't use that often, where booking two one-ways is different from a roundtrip.

So I'm always booking one-ways, not just because of that, but because sometimes I don't find the availability on the other leg. So when we were looking to book these flights to Japan, we were trying to book them right as the schedule opened. If I wanted to wait to book a roundtrip, I would have had to wait until the return leg opened.

And by then, maybe the outbound leg was already taken and there wasn't any availability. So we booked one-way trip to get to Japan. And then about 10 days later, when the schedule opened for the return flight, we booked those. So I'm booking one-ways. It gives you a lot more flexibility.

It's easier to change or cancel because if you have a roundtrip, sometimes you have to call and get them to split it into two items. So you can cancel one leg in case something better pops up or you want to change it. That's why I love one-ways. I say almost all-ways because there are probably two scenarios I can think of.

One, there are some airlines that might charge a fee both for canceling or booking an award flight. And so if they charge that fee based on the number of legs, then it doesn't matter. But if they charge it on a booking, then it might make more sense to book a roundtrip because you'd only pay the fee once.

Whereas two one-ways, you might pay the fee twice. And then the other one is there are some regions, and this is pretty common flying out of the UK and sometimes Europe, where if you have a trip that originates in that region, it might be more expensive. And so there might be cases where booking a roundtrip to Europe is slightly cheaper than booking two one-ways because the taxes and fees might be a little higher on the return.

This is one where I've read it. I haven't seen it in practice that often. So I'd encourage you to go look around, but it's not one that I would think too long and hard about. In fact, until finding it, researching this episode, it's not one I even considered. But now that I found it, I feel obliged to share it.

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And it is to look at trying to book your long haul flight, sometimes separately from the flight from your home airport or to your final destination. And the reason why doesn't always make sense. Sometimes I've found that the hardest flight to find award availability on is the easiest one for me to pay for.

And this has happened in the past where we were trying to get from San Francisco to Europe. And I could not find an award flight to get to Los Angeles to connect to the Los Angeles to Europe flight that was available. So I just booked Los Angeles to Europe.

And then we bought a paid flight from San Francisco to Los Angeles. Now, depending on the airline, if you see that San Francisco to Los Angeles flight pop up in the future, you can absolutely call the airline and see if they will add it on to your itinerary for free.

Maybe they won't, maybe they will. But at the end of the day, a lot of these positioning flights that either get you from your home airport to that long haul international flight or from your destination on the long haul international flight to your final destination, they're very inexpensive. So last year or the year before, when we were going to Europe, we wanted to go to the island of Mallorca and getting to Mallorca with points and miles would require me finding a carrier that flies from the U.S.

to Europe because there are no direct flights to Mallorca. But I would also have to find a carrier that flew to Mallorca. And of all the airlines and their partners that fly to Europe, I would guess that a small number of them also have flights to Mallorca from the airport they fly to in Europe.

So searching SFO to Mallorca was basically zero. There were zero flights I could find using points and miles. But searching SF to Paris and then coming home from Zurich back to SF was easy. We found amazing deals. And it turns out the flights from Paris and Zurich to Mallorca were like $50, $60 on Transavia and Condor.

So absolutely every time I'm looking for trips, I'm trying to search from a region to a region looking for those flights that can get me across the ocean, get me 90% of the way there. And that's one of the things that a lot of these tools do now is you can search for West Coast airports or USA to Europe or put in six or seven different airports if you're not flexible with all of Europe.

But I will flag one important thing. If you are booking flights separately, they're not on the same itinerary, you are not going to be protected if the first flight is late or you miss a connection or, you know, your bags aren't going to be transferred usually over. So you're going to have to make sure you leave time to collect them.

So that's just something I consider. Now, when I think about those positioning flights, if it's a positioning flight from my home airport to the airport I'm flying internationally from, I'm probably a little more risk averse and don't want to cut it too tight. Because if a flight's an hour or two late and then you miss your long haul flight, that could be pretty costly mistake.

Whereas if I'm flying from San Francisco to Europe and I have this connecting flight to Spain, I want to leave enough time that I can collect my bags and go through immigration. But the worst, worst case is that I might have to miss that flight. And if I can't get the airline to give me another one, I might have to buy another one and it might be a few hundred dollars.

But I'm not missing that long haul international flight, which is going to be a much harder thing to replace. So keep that in mind. And if you really want to be risk averse, you can code the night before or you can leave a really long layover. And fortunately, if you have the right credit cards, you can have lounge access and you can at least make that long layover a little more enjoyable.

Next tip is to take advantage of stopovers and open jaws. Now, if you're not familiar with open jaws, it's where you fly into one city and fly out of another. In a world where we're almost always booking one-way flights, it's not really a perk that matters because you could just book two one-way flights.

But if you're in one of those scenarios where you're redeeming points and the fees or the regions make it such that it's really more advantageous to book a round trip, but you want to hit up two cities, it might be very possible to book it as an open jaw.

And that is often allowed with programs. But again, if you're booking one-ways, it doesn't matter. So for example, if you were flying from your home airport to city one, added a stopover and then flew to city B, then you on your own went from that second destination and bought a flight or a train or a bus to third destination.

And then booked an award from that third destination home, you would actually be able to visit all three destinations with two one-way flights, one with a stopover, only having to buy that one flight in the middle. And like I said earlier, if that one flight happens to be very close together, maybe you'll get an amazing deal for under 5,000 points with a program like British Airways Obios.

So taking advantage of stopovers lets you hit two places in one. You can do it on the outbound, you can do it on the return. Many programs have a limit of one stopover, so you're not going to be able to stop 15 different times on your trip. But that's again where you can look and say which airlines are the best for stopovers, and you'll get a lot of answers, whether it's ChatGPT or just a search online.

The next tactic is mixed cabin awards. And this has both a pro and a con. So most of the times, there's actually no discount if part of your trip is in economy and the rest of it is in business. And so you want to make sure that you're keeping an eye on this because there are some websites where they'll say this is a mixed cabin award.

And if you don't look into what that mixed cabin is, so let's say you're going from San Francisco to LA to Japan. If that San Francisco to LA flight is an economy and the long haul is in business, that's great. That might be totally fine for you. But if the opposite is true and it says first class, but it's actually just first class to LA and then economy to Japan, that's going to be a terrible redemption of points.

However, where this can become valuable is sometimes those domestic legs are really tough to find in business class. And so if you can't find San Francisco to Tokyo in business class because you're only looking for 100% business class, you might be able to find an award where you fly in coach to a connecting city in Seattle or Los Angeles and then connect on in business class.

So that's something that's interesting and a way to book that positioning flight as part of the same award just in a different cabin. However, there are a few programs, I think Life Miles and Cathay Pacific are two, where they average out the award based on what percentage of the distance is in economy versus business.

So if you were flying from, I don't know, San Francisco to New York to London, and you're okay doing the San Francisco to New York in economy, but you really wanted to do the New York to London in business class, that actually might be one. If you booked through Life Miles or Cathay Pacific, you'd get a much lower price because they're going to average that out.

When I talk about hidden city ticketing, I'll talk about how this could actually be something you use to your advantage. Now, this next tip is one I use all the time, and it's that I try to book flights that will work, but maybe they're not ideal. And then I set up alerts to try to find the flights I really want.

And that gives me the comfort of knowing that the trip is booked. We don't have to wait until seven days before departure to know that we're actually going on this trip. So maybe you really want to fly business class, but you end up booking premium economy one way. Maybe you really want direct flights, but you end up booking a flight to change planes in another city because that will work, even if it's not ideal.

Maybe you really want to stay till Sunday, but you decide that you book a flight coming back Saturday because you found it. We do this all the time. And then most of these award search tools have the ability to set up alerts. To take my previous example, we booked two flights to Japan where me and one of my daughters is on one, my wife and the other daughters on the other.

But we have 11 months until we're leaving. So I went in and put alerts on both of those flights. So if two seats open up on either of those flights or if four seats open up on any other flight that day, we'll be able to easily cancel or change our flights so that we're all on the same flight.

And so I remember I told my wife, you know, yeah, it's not ideal that we're on two separate flights, but if I had to put odds on it, my gut says that there's a greater than 50% chance that between now and the day of departure that we are all on the same flight.

And very, very often a lot of these seats open up in the final days or even hours. Some of the searches I was doing today, kind of prepping for this episode, there was amazing inventory for flights that took off in the next 24 hours. It would be very stressful for me and my wife and the whole family if we were planning our flights and travel 24 hours out.

But if we know, hey, we're leaving this day, we've got two separate flights, but we're leaving this day. If six hours before I can change that flight to all four of us on the same flight, that doesn't really change anything because we were already prepared to leave that day.

Or if we were booked in premium economy and one hour before departure, business class opened up, which has happened multiple times because they open up this last minute inventory. I log on, change, move to business class, amazing. So if those kinds of changes happen last minute, it doesn't really throw us off the game.

It makes things better, totally fine with it. So one of the things I'm always doing, I'm booking flights that could work, setting alerts for better flights. Or if there's no flights that work at all, I'll set alerts. If we knew we wanted to go to Japan and I couldn't find anything, I'll just set alerts for all the West Coast cities flying to Japan for at least two people.

And I'll wait until I get an email and inevitably something will open up. And we actually did that because I was thinking, why not spread our options out? Now, obviously, sometimes booking multiple flights that you won't end up taking requires you to have more points and miles and have them in different programs.

So I get that that's not something that might be easy out the gate. And it's certainly not something where you'd want to buy points to be able to have backup flights. But the last tactic in this section is backup flights. And so if you have enough points and miles in different programs, especially now that a lot of programs have very, very flexible cancellation policies.

I will, every now and then, when I think it might be necessary, book a backup flight. We've all probably been at the airport in a scenario where a flight was canceled or significantly delayed. If you already have a backup booked and that backup can be canceled up until departure for no penalty, there's not a lot of reason not to do it as long as you don't need those points and miles.

And so I remember when we were coming back from Hawaii, I just booked a second flight just in case we show up and something was canceled and we wanted to get home. We had it. Turns out nothing was wrong. Canceled the flight. Got all the points back. Again, keep in mind, transfers to programs are irreversible.

So this doesn't work well if you want to make sure you keep your points as flexible as possible. But if you already have points, especially in programs like Delta, American, Alaska and United, where booking and canceling has no penalties and no fees, then this is something I use all the time just to make sure we're backed up.

I also use it for domestic flights with carriers like Southwest just to make sure there's another option if something were to go wrong. The next three things I want to talk about are things that kind of trip people up or can cause a lot of pain when you don't realize them.

And I talked about fees and program rules above, but I'm just going to focus on one specific one, and that's the fuel surcharge. And if you look at the list of fees, it's usually denoted by YQ, and I want you to make sure you're always keeping an eye out for this because not every airline charges it.

So if you're looking at an award flight and you see a really high fee, just like in that example earlier of the flight from Boston to Amsterdam, that doesn't mean all the partners are going to charge it. Now, if it's an airport tax, you're probably going to pay that everywhere, but if it's a fuel surcharge, you might not.

Now, British Airways, Lufthansa and Emirates are notorious for high fuel surcharges, and United and Air Canada are awesome in the opposite direction in that they aren't charging those extra fuel surcharges. Most of the award search tools will show you these fuel surcharges, and many of them even have the ability to limit the amount of fees.

So you can say, hey, I want to search for flights from the West Coast to Europe, but don't show me anything if the fees are more than $500. Now, keep in mind that high fees aren't always bad. In that example before, if your option is a $2,700 cash price, a 240,000 delta mile, or a 47,500 points plus $1,000, well, that $1,000 fee might feel like it burns, but it's way better than paying $2,700 to take that flight.

Now, in that case, the flying blue option was way better, but in general, I would say just make sure you're accounting for those taxes and fees when you try to decide whether something was a good deal. Another important one is when you have those taxes and fees, there are credit cards that will extend all their travel benefits if you just pay the fees on that card.

So the Chase Sapphire Reserve is one of the best ones here. You've got to go look at your card's list and guide to benefits. But with the Chase Reserve, even if you just pay the taxes and fees on the card, all those extra travel benefits, whether it's delayed flights, lost baggage, anything like that is going to be covered just by paying those taxes and fees.

So make sure that you pay the taxes and fees on the right card so that you're covered for all the travel protections on that trip. This episode is brought to you by GELT. Now, when it comes to building wealth, taxes are such a big part of the strategy. And as tax time gets closer, getting prepared now is so important.

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Now, the last one here is around hidden city ticketing or married segment logic. And the way this shows up is you might find a flight from, let's call it, Washington, D.C. to Paris and then connecting to Nice on Air France. And Air France, Americans, Swiss Airlines are the airlines I've seen this happen most on.

And you'll find that flight available with points. But maybe you don't want to go to Nice. So then you just search D.C. to Paris and you can't find it. And so for reasons I don't always understand, airlines can kind of marry these segments together and say this flight is only available with points and miles if you take both segments.

This also happens with cash tickets. So there are times where flying from Denver to San Francisco is way more expensive than flying Denver to San Francisco and then connecting to Redding, California, for example. And there's a whole website called SkipLagged that makes it easy for you to search and say, hey, I'm looking for flights from city A to B.

Show me all the flights, even if they connect through B and go on to some other city. But there's a couple of things to keep in mind. One, if you check bags, almost always your bags are going to be checked all the way through. So you don't want to check bags on flights like this.

If you schedule a layover and that layover is overnight, or if you're on an international flight coming into the U.S. and you left from a city that doesn't have you clear customs and immigration in the foreign country, then you're going to have to collect your bags and go through customs and immigration.

So there are cases where you might be able to have your bags only be checked to the first destination and not worry about that. But in general, most people say, if you're going to do this, don't check bags. They also say, if you're going to do this regularly, don't put your frequent flyer number on your ticket because airlines don't love when you do this.

If it happens one time and you get off the flight and send a message to the airline and say, something came up, I have to cancel this flight. I'm not going to be going on to Nice or I'm not going to be going on to Redding. I don't think it's going to be a single problem if you just do it one time.

But I think if you make a regular habit out of this, airlines will be upset. The good thing is if you're booking flights with points and miles, you're not going to earn points and miles on that flight. So having your frequent flyer number attached maybe doesn't matter. Most frequent flyer programs preload your profile with your frequent flyer number and don't let you change it.

However, if you're booking your partner or, you know, your kids or your family members, they usually don't require you to attach a frequent flyer number to additional travelers. So you can always just create an additional traveler that has your name and date of birth. And instead of using I'm traveling, you say, hey, the other Chris is traveling and that Chris doesn't have a frequent flyer number attached.

And that might be a little bit easier, especially in a situation where having your frequent flyer account doesn't actually add anything to the trip or scheduling a really long layover. Again, if you were flying to Paris and you had an overnight connection, you could probably make a case that you want to only check your bag to Paris because you're going to have to go stay at a hotel and you need your things.

So definitely something to try out. So you can also turn this into a hack. If you remember what I described with mixed cabin awards, Avianca, Cathay Pacific, if you have some economy legs, it might be cheaper. So imagine you were looking to fly from San Francisco to Japan and then you had an onward flight to India.

And maybe with a carrier that has regional pricing, whether you fly to Japan or India is the same price. But that Japan to India leg is entirely an economy. It might actually bring the entire cost of the ticket way down because it's only half in business and half an economy.

But again, you want to make sure that your bags aren't going to end up in India because that would be a massive challenge. There is a episode of the Frequent Miler podcast where they talked about all the different ways that you can actually fly further to save miles. I'll link to that in the show notes if you want to go deeper.

They're kind of 301, 401 advanced hacks when it comes to this stuff. They probably go beyond anything I've ever even done. But for the adventurous person that wants to go down that rabbit hole, I will share that link. Next, I want to talk about hotel tips. And this one's pretty quick.

There aren't as many tricks and tips for hotels. However, Hilton and Marriott offer fifth night free. So if you're booking your stays in groups of five nights, you can get about 20% off. It's based on usually the cheapest of the nights. So if the nights fluctuate in price, it might not always be 20%.

But if they were all consistent, you'd get one of five nights free. And then if you have an IHG card, you get the fourth night free. So 25% off, assuming they're all the same price. Hyatt and Hilton also don't charge resort fees on award nights. And so when I went to San Diego the other week, the hotel had a $42 a night resort fee.

But because I was staying with points, they waived that fee. Hyatt also waives that fee if you're a globalist. So there are multiple ways to get that resort fee waived. Also, if you have the Hyatt business card, you get 10% back on your points bookings. After you spend $50,000 a year, you only get up to 20,000 points back.

So I'd say it's a small benefit relative to the cost of spending $50,000 on a card. But it is a benefit nonetheless. So that's a couple of the hotel tips. In general, there aren't as many tricks and tips for booking awards for hotels. But I will say those Hilton free night certificates are amazing.

Hyatt suite upgrade awards are pretty amazing because you can actually confirm at booking a suite. We've used those a few times, especially now that we have kids. And that has made travel with hotels using points way more relaxing and stress-free than having everyone in one small room. Finally, two quick niche hacks.

One again on kids is that different airlines have different pricing for lap infants and children. Now we don't have lap infant aged kids anymore. However, when we did, it was really surprising how different the pricing was. And sometimes it was so different that it was worth paying a little bit more for the adult ticket in order to get a way better deal for the child.

And that's because the price can range wildly. So for example, Air Canada, $25 or 2,500 points. British Airways, 10% of the mileage of the trip. But Delta and a lot of other carriers are 10% of the adult fare. And so just because you booked with points and miles doesn't mean that the adult fare might not actually have been way more expensive, especially in the case of one-ways.

So I think we did this one time and we were looking at Air France and the adult fare on Air France was only 50,000 points. But the adult price, if you paid cash, was like $7,000 as a one-way ticket. So the lap infant fee would have been $700. Whereas if we had booked that same flight on Air Canada, it would have been $25.

Now, Air France and Air Canada are not in the same alliance. So I couldn't have booked that exact same flight. But as an example, there might have been other Sky Team carriers that had way more reasonable lap infant pricing. So I'll link to a post in the show notes that talks all about lap infant pricing.

But if you're traveling with a lap infant, be careful. And then if you're traveling with children, there aren't that many programs that give you a deal. But Air France and KLM is hands down the best. For kids 2 to 11 years old, you just get 25% off the award price.

We've used this before. It's awesome. If you're traveling with lots of children, Air France and KLM is going to be an amazing option to save points. Cap Portugal also does 25% off kids, but I'm not actually sure how old they have to be. But that's one thing to look into.

There aren't a ton of programs that do this. But if you can save 25% of your miles, why not do it? And it's automatic. On Air France's website, as soon as you put the ages in, it's just cheaper flights. Finally, the last tip here is to take advantage of the Southwest Companion Pass.

It's one of the best hacks out there because you can earn it without having to even fly the airline. Obviously, if you don't fly Southwest, it doesn't do you any good. But you can earn it entirely from credit cards, from credit card welcome bonuses. From shopping portal spend and stuff like that.

And if you hold a Southwest card, you automatically get 10,000 points towards that status without any spend. So normally, it would take 135,000 Southwest points. With a credit card, it takes 125,000 points. And once you hit Companion Pass, in the year you hit it and the following year, you can nominate a person that you can change, I think, up to three times.

And that person can travel for free with you. You can confirm it at booking, and they just have to pay the taxes and fees on the flight. So we've had this in the past, and it's not quite two for one because obviously, you have to pay the taxes and fees.

Though domestically, those taxes and fees are $5.60. So it's pretty close to two for one. But even internationally, if the taxes and fees are $50, it's an amazing deal. And it's possible to earn it with welcome bonuses. So you could open up a business and personal card. And usually, those two welcome bonuses combined are more than 125,000 points.

Or you could open up a card during some of the times they do promotions where the welcome bonus can go up to as high as 120,000 points. And because that welcome bonus usually requires you to spend 5,000 points, you get 5,000 from the spend. You get 120 from this signup bonus.

And now you've already hit companion pass. So I say, if you're going to try to go for this, going for it in January, we'll get it for that whole year and the next year. But be careful that as soon as you hit the spend, it will show up on the statement that closes.

So sometimes they have these great promotions with huge welcome bonuses in October, November, December. You really want to make sure you don't hit that welcome bonus at the very end of the year because then those points will post in the year before. And you'll only get companion pass for that year and the following year.

Whereas if you hit it in January or February, you'll get it for the entire year plus the next year. And because signup bonuses count, it makes it very easy to get. Or you can just get one big signup bonus and spend a little more to get there, fly a little, use the shopping portal, et cetera.

But keep in mind that if you're going for status on Southwest, A-list, A-list preferred, the credit card welcome bonuses and every dollar you spend on the credit card doesn't count the same way. The amount you have to spend to get those tier qualifying points is a very different formula.

And so you could find yourself at companion pass on Southwest and having only gotten a thousand points towards getting status on Southwest. So that wraps it up. That's 18 ways that I think you can really dial in your award travel and book some incredible flights for you and your family.

And I really hope this is helpful as always questions, feedback, thoughts, podcast at all the hacks.com. That's it for this week. I will see you next week.