S3, E17: What It’s Like to Use a Concierge Service to Book Award Flights

In this episode of Unpacked, host Aislyn Greene turns to Award Magic, an award-booking service, for help dealing with travel points and miles.

Booking travel using points and miles can be complicated. Some people love the challenge; others dread the task. This week on Unpacked, we explore a service that does all the hard work for you, so you can just focus on your best travel life.


Aislyn Greene, host: I’m Aislyn Greene and this is Unpacked, the podcast that unpacks one tricky topic in travel each week. And this week, we’re looking at a (much) easier way to book travel using points and miles.

If this topic seems familiar, it’s because last year, we ran an episode about points and loyalty programs. I spoke with Paul Rubio, who is Afar’s points and miles specialist, about the best credit cards to earn points and the best ways to maximize those points. He’s fantastic and I put a few of his tips into play in my own life. And then a couple of months ago, I started to plan for a trip to Japan that I wanted to book with a bunch of Chase points I’ve been collecting. So I did some research, started to noodle around . . . and immediately, I wanted to give up. I just did not want to spend my time doing this. So I kind of stopped, I put everything aside for a bit. And then in our Where to Go This Summer episode, writer Mark Ellwood mentioned a company called Award Magic that he has paid to do all that points booking for him.

So I reached out to owner and CEO Brian Cohen, who shared how he got into the business, how his services work, and yes, agreed to help me book my tickets to Japan, though in a rather surprising fashion.

Brian, welcome to Unpacked. It’s so nice to have you here today.

Brian Cohen: Thank you.

Aislyn: You have a great business name, Award Magic. Would you mind telling me what it is and what it is that you do?

Brian: Sure. So, I like to think of Award Magic as the best way to help you earn and use your credit card points to travel around the world. And that could be standard economy tickets or if you really want to go high class, to help you get those business-class flights for less than you might pay for an economy ticket.

Aislyn: I love it. Which I’m very eager to do later on in this chat, but I’m curious to know, how did you get into this business? Like, are you just one of those people who loves, you know, points and miles and maximizing them?

Brian: So I am now, certainly. I was a bit more hesitant and trepidatious when I first learned of this. I was sitting at a lunch with a group of friends. A new guy sits next to me, casually mentions his 46 credit cards, and my interest is piqued. I turn around, I say, “What are you talking about? I need to know more.”

And he said, “It’s Shabbat, so I don’t want to talk about it, but let’s go out for drinks.” And so I took him out for drinks a couple of times. This was like 2014, early 2014. And by the time he finished explaining to me, I had blogs I was reading, websites I was going to every other day, credit cards I started signing up for—I just got my, I think 39th of like this time period a couple of weeks ago. I think I’ve had about 90 or a hundred over the past 10 years.

And I just love learning how to use them, learning the changes that happen. And I’ve been doing this for myself and friends and family since then. So I’ve gotten a chance to fly business or first class to Australia, Singapore. My wife and I just had our honeymoon, went to Japan, the Maldives, South Africa. I mean, we like to travel places, so yeah.

Aislyn: Yeah. Wow. It just sounds like you are uniquely suited to this as well.

Brian: I was a math teacher when this was going on. I taught high school math for 14 years and I’ve always tried to figure out, like, “What are the rules and how can I express them to people or explain them to people?” And I realized I also like to navigate around them. I always thought I would make a really good accountant if I tried. Uh, so this is my version of that. I’m accounting for points. That, that’s my concept.

Aislyn: And how did you transition into doing this for other people, going beyond friends and family?

Brian: So it was fortuitous timing. I was leaving the classroom, moving from Brooklyn to Baltimore, and I was looking for something else to do. Uh, deep COVID teaching was not quite fun, especially in New York where I was living. So I wanted a break from being in person in front of students for a while. And a friend of a friend just happened to be selling his company that he started back in 2011.

So I thought, “This is the best time to experiment.” I bought it, got a great deal. Of course, you know, it’s a great deal. And, uh, everything he said would come true has and even more so. I’ve tried to expand it. I’m trying to get into, like, the honeymoon industry. Trying to do a lot of these round-the-world tickets we can talk about too. I mean, it’s been really fun.

Aislyn: Yeah. And you have a really fun backstory: the reason that you want to get into this honeymoon business. Would you mind telling me your personal story?

Brian: So I got married in May of 2023. Uh, we’re almost at one year here. And when I was getting ready for the wedding, I was talking to my wife about the business that I had bought—with her suggestion and assistance—I should add. And we basically strategized with ourselves and our parents, “Which credit cards should we try to sign up for and then pay for parts of the wedding with so that we could all earn a whole bunch of points that we would then use for future travel?”

So my mother-in-law paid for a bulk of the hotel expenses that we stayed at. And I got her to get this Marriott credit card because it was a Marriott hotel. And now she has, I don’t know how many hundreds of thousands of points because of that. So she can stay at hotels for free for the next, like, five years because of our wedding.

Aislyn: And then you were able to take how long of a honeymoon because of these points?

Brian: So we were in 10 countries over seven weeks and, because we had a short engagement—we got married in May, we got engaged the prior November—we didn’t really plan much. By the time we left the United States, we had a plane ticket to Japan, a plane ticket home from Frankfurt and five hotel nights in Tokyo. But everything in between those seven weeks was basically unplanned. So as we went, we decided, “Oh, where do we want to go next? What points do we have to get there? What are the best deals to use those points for?” And I just did my magic, I say.

Aislyn: Well, I would love to talk more about what it is that you do. Because, as someone who does not necessarily want to spend all my time learning about points and miles and credit cards, I was so grateful to find out about you. You were actually recommended by one of our travel writers. So what kinds of services do you offer? Like, how does that work?

Brian: I try to separate it between the earning side and the spending side. On the earning side, I run workshops now about once a month. I have an introductory workshop for those folks just curious to start. The next one, I think it’s coming up at the end of May. And I have a novice level one that I do for people who’ve been doing this for a while, but they want to know a bit more about the tools that we use to try to help book things so they can use it for themselves.

And, uh, I also do one-on-one or small group consultations. That if you want to know the credit cards you currently have, how should you be maximizing their use? Or if you want to change credit cards or you want to learn about—my God, there’s a whole rabbit hole of things you could do to earn points—um, I’m, I’m happy to talk with you about it.

And then on the spending side, if you just don’t want to spend the time yourself, you have 400,000 Chase points for some reason, or 300,000 American Airline miles and you want to go somewhere, you can contact us and say, “I live in Chicago, I want to go to Venice” or “I live in Miami, I want to go to Singapore. These are the points that I have, can I get there in business class, ideally with those points?”

And myself and my staff will go in, analyze. We do a whole bunch of searches with various tools. Sometimes it’s just the airline directly. Other times there are these search tools that have been coming up over the past several years. Try to find the best options, display them to you, you choose which ones you want, and then we will go into your account—with your permission, of course—book them for you so that you don’t have to spend the time. Our motto is basically maximize your points, minimize your hassle to help you get where you want to go.

Aislyn: And would you mind running me through the, the various fees? Like, what do you charge for say, one of the classes versus, you know, time with you like this?

Brian: Sure. So, a class could be $30 or $40 for an hour-long class. Small group, I max it out at 20 people, maybe 25 depending on the day, uh, so you have a chance to ask questions towards the end. If you want to do a one-on-one consultation, that varies between $150 to $350 depending on the type of consultation and all that’s displayed on my website.

On the spending side, if you want to work with my staff and communicate over email, you pay a $40 search fee. And for a standard round-trip flight we might help you book, it would be $225 per person, but that search fee is then deducted from your final invoice. So $450 bucks in total, you pay $40 upfront for two people.

Um, if you do want a bit faster service, I offer something called AM First Class, where you’re guaranteed to work with me. I will call you, text you, email you, whatever you want—or not, I don’t have to badger you. Uh, and that’s a bit of a higher price point. You pay a $100 registration fee once. And then every time you book a flight, it’s more expensive than the standard tier, [it] is around $325 a person for a round-trip ticket.

Aislyn: If people—like, say, you know, they go through this process, but they’re not happy with the flights and that’s all that’s available. Like, how does that work?

Brian: Yeah, for the standard tier, that’s the $40 search fee. So that is not refundable. It’s just a deposit, basically saying, “I actually want to contract with you for your services.” And, if we don’t find anything that they like, then they’ve only used $40 and that’s it. If they do say they like something, then they pay the rest of the fee.

And for my services, for the AM First Class, anybody who wants to work with me directly pays the $100 registration fee and then tells me where they want to go. But after that registration fee, they no longer have to pay me to do a search. I will just do a search for them whenever they ask, but when they eventually book with me, it does cost more. That’s the trade-off.

Aislyn: Got it. And what has the reaction been? Like, how have people responded to what you do and, and how do you see them coming to you? What, what do they want?

Brian: So most people I talk to have no idea this exists. And they say, “Oh my God, that’s amazing. Can you please help me get to Iceland next week?” You know, that, that kind of response. The folks who are somewhat aware of points and miles, they’ll say things like, “Oh yeah, I’ve heard of that.” Or “I’ve done a couple of things myself, maybe I’ll ask you for the really hard stuff.” And, you know, they come around a couple of months later and say, “I was trying to get to Japan, I just, I just can’t, can you help me?” And then I try as best as I can.

Aislyn: Amazing. I mean, what do you think is the biggest challenge around points and miles or maybe multiple challenges?

Brian: The biggest one’s probably the devaluation of points over time and the restriction of what are called award ticket seats. When you use your mouse to book a flight, that’s an award ticket. So, it used to be, you know, 10 [to] 15 years ago, it was much easier to find open award seats because airlines wanted you to find them. But there were fewer miles being doled out. So it was kind of this back and forth.

Nowadays, there are fewer seats available. So you really have to know when they come on sale, what’s the best use of the points to book them when they do. Uh, but you can earn way more points. The credit card I just signed up for is a 250,000-point signup bonus, which is the biggest I’ve ever seen for it. And literally three days after I got approved, they upped it to 300,000. So, inflation—

Aislyn: Oh my gosh.

Brian: —devaluation, increase applied. I don’t know, but like, I definitely want the points. So I signed up for it.

Aislyn: Sure. OK. What is that card?

Brian: It’s the, uh, American Express Business Platinum card. And it’s an interesting story because Amex does all these targeted offers that maybe you’ll get it, maybe you won’t. So I was actually trying for three weeks on their website from four different browsers in private mode. And every time I went there, I only got 190,000-point bonus offer.

But since I read these things, I knew there was a bigger one out there. And it took until my wife and I were actually coincidentally sitting in the American Express Centurion Lounge at Philadelphia International Airport. I open my laptop, sign on their Wi-Fi, and boom, there it is.

Aislyn: So that’s the secret. You just have to be in an Amex lounge. That’s amazing. Well, we’ll get into this a little bit when we talk about my specific situation, but how does the process work when somebody is working with you or someone on your team to book a ticket or ask you guys to do the work?

Brian: Fairly straightforward, you just contact us through a form on our website, or if you want to, you can book time just to chat with me about how our company works. Once you submit the form, we do a bit of an intake process to make sure we have known what you’ve asked. Sometimes people type something incorrectly, [we] want to make sure we have the right details.

And once that’s done, if it’s with my staff, one of them is assigned to work with the client and then they start emailing back and forth, booking things, et cetera. If it’s with me, I’ll usually send an email back saying, um, “I’ll be ready tomorrow, I’ll send you a text or call you if you want, and here will be some options, et cetera.” So once that back and forth is through, the client says either, “No, none of these options work for me.” And then that’s it. We’re done. Thank you. Move along.

Or if they like the options, they say, “Yes, book me option one for the outbound, option three for the inbound.” We send a whole host of instructions of what to do, which could be as simple as, “Just please share your Alaska Airlines login information and we’ll book it.”

But normally people have what’s called transferable currencies—that’s what I’ve been referring to, the Amex Membership Rewards points, Chase Ultimate Rewards points, et cetera. So we give instructions of how to transfer those points so that people don’t get lost in the process.

Aislyn: Well, where do you hope to take your business since it’s relatively new to you? Like what do you envision going forward?

Brian: So it’s interesting you asked that question. Uh, I’ve never thought about what work-life balance would look like, because when I was a teacher, it was kind of forced upon me, I have to do all of these things. And now that I’m a small business owner, I get to choose what I want to do. And I really enjoy, you know, booking flights for people. So I think I’ll continue to do that and try to advertise for just the simple New York to—I don’t know—Serbia and back those kinds of flights.

But I also really like doing round-the-world tickets, which is a particular airline, All Nippon [Airways] based in Japan. They have this amazing deal where normally a business-class flight just to Europe will be, let’s say 70,000 points one way. So for 145,000, roughly, you can get up to 12 business-class flights around the world. To me, that’s amazing. And, uh, every time I book that for people, they’re so appreciative. So I want to do that.

And I’m specifically hoping that maybe if I work with folks on their wedding planning, that that could be people’s honeymoons, that I come up with this niche, helping them figure out which credit cards to use, they earn these points in particular, and then I helped them get these round- the-world tickets. That would be amazing, if that was my business.

Aislyn: Well, I look forward to seeing how that plays out. I was curious, you know, there are services like Point.me and how do you see yourself as different from a service like that? Or do you see yourself as different?

Brian: So some of those services are similar to me, Point.me has its own concierge service, which is somebody helping you book award tickets. So it does overlap. I think there’s enough market out there that none of us are taking too much, especially since every time I tell people what I do, 80 percent of the time they say, “I had no idea that existed.”

So, there’s room to expand. And most of—I think most of the money—they make is from their search engine, which I’ve used. I’m not as big a fan because it takes so long to perform one search and I do searches all day long, so I can’t waste my time. But there are the people who might want to do it themselves, I think, “Sure, go to Point.me.” And in my introductory workshop, I talk about them. I talk about other companies like AwardLogic, PointsYeah, Seats. aero, and I tell them what are the pluses and minuses of these things. And if you want to spend your time doing that, certainly. If you don’t, then you come to people like me. And I’m happy to help people do it without them having to bother.

Aislyn: Well, that’s a great segue into my particular conundrum, which I will lay out for you. I don’t know if it’s been smart or not, but my partner and I have been saving our Chase—we have the Chase Sapphire and Freedom cards, and we’ve been saving those points for a few years now. We have—I just logged in and checked my account today—we have 312,779 Chase points. We have 6,620 Hyatt points and we have 38,531 Marriott points.

So our goal is to go to Japan this fall. I actually get to take a six-week sabbatical from work ’cause I’ve been here for 10 years. So [I] want to spend a bulk of my time in, in Japan and I’d love to fly us both business class there and back. So my hope was to use those points, or at least some of them, at least the Chase points for flights and then, you know, maybe do something with the hotels with the other ones, but what should I do?

Brian: So this is a great problem to have. And people come to us all the time and they say, “I want to go to Japan,” because it’s a valuable destination. Maybe because during COVID they were on lockdown longer than other countries. So there’s pent-up demand. I’m not going to lie, before COVID, I had two tickets to Japan, they got canceled twice. So when my wife and I went on our honeymoon, I was particularly enthused to get over there.

And I got to say this upfront: It is hard to get award tickets to Japan. If you want to fly economy, it’s mildly easy, but still, you might have to do a stopover here or there on the way. Some folks have to go via Europe to get there, which is adding a lot of time. If you want to get to Japan, you have to do one of two things, well, really one of three things. Either you book your plane ticket about a year in advance, and by that I mean 355 days or 360 days, depending on the program, I’ll talk about that. Or one to two weeks in advance. Or you get incredibly lucky.

Aislyn: Oh dear.

Brian: So I’ll tell you our story and how that applies to you.

Aislyn: OK.

Brian: So we knew we wanted to go to Japan and I told my then-fiancée, like, “We’re not going to get these tickets in advance. Let’s just plan it as we go and see.” There are so many flights to Japan from New York, Boston, Dulles, Seattle, San Francisco, everywhere in the country, all these major cities. At least one of them is going to have two business-class seats within a week or two of departure. That’s consistent.

We were lucky. Three weeks before we knew we were leaving, I saw two Japan Airlines flights departing from Seattle. And I thought, “You know what? Let me book those two.” And we did, and there was no other worry on my mind, but that was lucky.

In your case, you may not be able to do what we did because we had American Airline miles and Alaska miles. You don’t have those. Here’s the deal. There are two major airlines that fly between the U.S. and Japan. Japan Airlines, the one that we took, or JAL. And All Nippon [Airways] or ANA. To book JAL flights, you can use anything within the OneWorld Alliance of points, the best option of which is American. That’s the one that I used. You can also use Alaska miles, or in your case, you could use British Air miles, which you can get from Chase. Chase transfers to British Air one to one, right?

Aislyn: Oh yeah, OK.

Brian: To book ANA, that’s part of the Star Alliance, you have to use the Star Alliance carriers, which would be, in your case, United, Singapore Airlines, Air Canada. But what’s interesting with ANA—and this is the one that I think I’m going to recommend—they have this really special deal with Virgin Atlantic. And it sounds crazy, but you can use Virgin Atlantic Miles to book an ANA flight as long as there’s availability. And that’s the crux, right?

So what I do when I try to book those flights—it’s gonna sound convoluted—I go on the United website, I search for whatever flights I can find between the U.S. and Tokyo, because the United website will show ANA flights. If I see an ANA flight, then I tell my client, “Let’s transfer your points to Virgin Atlantic, call Virgin Atlantic, because you can’t book it online. Tell them which flight we saw on the United website. They should see it on their system and then book it for like half the miles.”

Aislyn: What!

Brian: So the numbers we’re talking about in case you’re curious, because you said you have 312-something thousand Chase points. If you want to book an ANA flight with United miles, it costs 110,000 points per person in business class to go one way. You’re not going to have enough for that.

Aislyn: OK.

Brian: If you booked it with Air Canada, which you can also transfer from Chase, it would be something like 75,000. That you would have enough. But why waste the points? If you book it with Virgin Atlantic, we’re talking 50,000 points one way. So you’ve gone from 110 [thousand] per person one way to 50 [thousand]. And so let’s say you do end up getting that flight, 50,000 times two for you and your partner, there and back, that’s 200,000 of your Chase points you’ve used. You still have another 112,000 left, which I would recommend using at a Hyatt hotel in Tokyo, which is what we did.

Aislyn: Yes. Yes. Let’s do it. How long does it usually take to kind of book these, like, how long does this process usually take?

Brian: With someone who’s ready to go—like, it sounds like you could be ready to go—the process might take a day or two. I got a booking request on Monday for someone who wants to go to Italy. I finished her up today. But for people who are a bit more, uh, prescriptive, they want to do a certain airline, a certain day, et cetera, that might take a couple of weeks and at some point we will tell them, you know, “This is actually taking more time than we have and our service is not unlimited. So unless you want to take one of the options we presented to you, it sounds like the answer is no.”

So that sometimes happens for places like Japan. If people are booking seven months in advance, which is, you know, not a year and not one week in advance, we’re probably not going to find exactly what they want.

Uh, I did once book a guy, I think for him and his son from JFK through Zurich to Tokyo using Air Canada miles, but flying on Swiss Air. That’s one of those cool partnership things again. And he was very happy with it because he’s getting to go to Japan, even though he would rather do New York–Tokyo, nonstop, but that wasn’t available.

Aislyn: Sure.

Brian: You know, so that happens sometimes. And, and for you, I mean, if you’re willing to wait last minute, then, I’m like 95 percent positive we could get tickets for you using Virgin Atlantic miles. There’s always, you know, some give and take, but some folks are not willing to do that, and so they have to do something else instead that uses more points and maybe goes through Europe instead.

Aislyn: Ooh, that’s such a tricky—like, there’s this part of me that’s like, “Yeah, let’s wait for the you know, the best possible option.” But then it’s like, “Well, what if there was that 5 percent chance that something doesn’t come through and then, and then what, you know?”

Brian: What I have done for myself in the past: There was one time I went to Australia. I had, I think, Qantas first class booked on the way there. But I couldn’t find anything on the way back and Australia is also hard to find. There, you almost can’t get 12 months in advance because they don’t really release a lot of award tickets. But if you want to go on one or two weeks’ notice, again, like, that’s really easy to get to Australia and New Zealand. So I set up an alert for myself that the day that I wanted to depart to find seats to go back to America. Literally when I arrived—I think I flew into Sydney and then took a connecting flight to Brisbane, when I was on the train from the Brisbane airport to downtown—I got a notification on my phone: two seats, Qantas business class for the return. And you better bet by the time I arrived in the train station, those two seats were booked.

Aislyn: So that’s something that I could do is, like, set up an alert in that way. Or would you guys handle that? Like say you were working with a client who decides to not book now and wants to wait to the one to two weeks’ mark.

Brian: Great question. So I actually had, uh, I did around-the-world booking for three gentlemen from Reno and they—I think they’re in Japan right now. Yeah, they’re in Japan right now—and when I booked it for them, I told them the same thing I told you, that I am 95 percent sure—let’s say I book you a ticket on ANA economy home, and there’s a convoluted reason why I had to do that. You can upgrade those tickets for free with the way the round-the-world ticket works. So I said, “I will start checking two weeks before departure and see if there’s an upgrade that I can get you on.”

No joke, the first day I started looking, I found one. I texted them when they were in, I don’t know, Osaka or something, and said, “Is this a good enough flight for you?” And they said, “Yes, go for it.” And half an hour later they were upgraded. So their flight home, I think, is in five days and they’re doing ANA business class to L.A., I believe. They’ll be very happy.

Aislyn: That sounds fantastic. I think I would be willing to—so, if I were to wait, you know, the one to two weeks, would you do the same thing like book an economy or two economy tickets and then look for those upgrades? Is that how it would work?

Brian: So that was specific for the round-the-world ticket for this situation. Uh, I might recommend trying to just have, like, a cash ticket purchased that was refundable. So, you know, if you can’t necessarily get business class, you are willing to do this cash ticket. You have something on hand, but you could cancel that cash ticket.

Either if you pay the full fare for a fully refundable ticket, that might be more expensive, but you get your money back or you pay less money and maybe you pay a fee of like a hundred bucks per person to cancel the ticket, but you’re willing to do that because that means that you get business class to and from Japan. So I’ve done that for clients before, too, where they book something and then I start looking two weeks in advance, they cancel that thing and I book a flight for them and we’re all happy.

Aislyn: OK. Well, I mean, I would love to see what is available now and then consider the possibility of waiting if that’s, if you’re open to that.

Brian: Could you remind me what were the dates? And, I don’t remember where—you live on the West Coast somewhere, right?

Aislyn: We live in San Francisco, or in the Bay Area. So we usually fly out of SFO, but, you know, happy to fly out of LAX or Seattle or wherever. I think our time off is from, so we have about October 5th, October 5th through October 27th-ish.

Brian: OK. Just going to do a quick search on my United site here.

Aislyn: Great.

Brian: Yeah. As expected, everything is 200,000 miles apiece plus.

Aislyn: Oh my God.

Brian: But to prove my point, let’s go back to May [2024]. Let’s see what’s available in May.

Aislyn: OK, cool. This is great.

Brian: Yep. There we go. You could go San Francisco–Osaka, business class. What day is that tomorrow? Let’s see, you could do San Francisco–Narita, also on the 3rd, so on Friday you can fly out. And actually, I think there’s a couple of planes that ANA has that have their new business-class seat called the Room, which is a way nicer seat. It’s—I mean, business-class creep is a thing. It’s getting closer and closer to what first class used to be—and now first class is like literally a living room on a plane in the sky, which is incredible if you can get that.

So this flight, I think you could get—right now there’s actually, it’s a bunch of bonuses from Chase, American Express, and Capital One, 30 percent bonus to Virgin Atlantic, so the number I said to you, the 50,000, like, cut a third away from that, and that’s how many points you could pay for a flight that should cost like $7,000, you’d pay like 38,000 points.

Aislyn: That’s amazing.

Brian: So I think, I mean, the way that I would play this is just to, like, recap that right now, I suppose, where I would describe: I did a search from San Francisco to Tokyo and all that I found for October was, as expected, very expensive flights. But if you look in the next two weeks of the calendar, you’ll see there are plenty of business-class seats available between San Francisco and Tokyo.

Aislyn: So if somebody really wanted to book now, could we play it a little bit as though I wanted to do that so we can show what that looks like?

Brian: Yeah, I mean, I did this this morning with a client. I said, you know, “You need to transfer these points. Now, give me the login information for your account. I’ll go into it.” Or in this case, I’d have to call on your behalf.

So sometimes with Virgin Atlantic, actually, if your account, because you have a stereotypical female voice, I have a stereotypical male voice, I would have to call and have you on the line, authorizing me to book flights for you. And then you could hang up and I would talk to the agent basically. So what I do in those cases is sometimes Virgin Atlantic has a hold time of, like 15ish minutes, so I call first and then once I get the agent, I call the client—in this case, you—do a three-way call, you would authorize me to talk on your behalf. Then you hang up and I take care of the rest.

Aislyn: Got it. And if, say I, or, you know, someone wanted to do the Virgin Atlantic points, so would a flight right now still cost the 50,000 per person per flight? Or was that applying to future if you waited till one to two weeks in advance?

Brian: Uh, that’s going to be one to two weeks in advance or, you know, 350, whatever, plus days in advance. Uh, if you, and that’s only for—OK, there’s a clarification here. Any of these airlines that are releasing award tickets, they release them in different tiers, or fare codes, we call them. So United has its own set of fare codes. So when I was looking at October, I was seeing, I think YN or ZN or something, whatever it is, which means it’s, you can only book it with their points. It’s going to be more expensive.

It’s not what’s called the Saver Award level. For the Saver Award level in business class, you’re looking for a code of I or J generally. And so right now when I’m looking at their website for May 3rd, it shows the codes, it says “United business I,” “ANA business I,” and so I—haha—know that if it’s in that Saver category, both Air Canada and Virgin Atlantic will also be able to book the same ticket because it’s now Saver for everyone. Does that make sense?

Aislyn: Yes. Yeah, it does. So if, if, like I wanted to book now, basically we wouldn’t have enough points. We’d have to use points for some part of the trip and then the rest we’d have to pay out of pocket.

Brian: Exactly.

Aislyn: OK. Well, I guess we’re waiting.

Brian: Yeah. Since you have Chase points, they do transfer to United, but you’d have to spend 200,000 points for one of you to go one way in business class. That’s not worth it.

Aislyn: Absolutely not worth it. OK. Well, we, I think we’re, I think we’re going to wait. We’re going to test this out. It’s kind of thrilling, but also terrifying. So it sounds like we’ll be connecting in mid-Septemberish about this. So if I wanted to book some hotels using points, how would you recommend that I balance that out and save enough of my Chase points?

Brian: That is a good question. OK, between May and October, I’m trying to think of a couple of different things here. I do think Chase transferring to Hyatt is the best option for hotels these days because it costs so few points. Like my wife and I now every, her birthday’s in February, so every February we go to Cancun to, like, an all-inclusive and you can get all inclusive for, like, 23,000 points a night for two people, when you would spend $700 a night for the same place. So it’s such a good deal.

When we were in Tokyo, we stayed at the Hyatt Centric Ginza Hotel, I believe it was called. And I think it also costs 25,000 Hyatt points a night. So that’s what I would suggest, like taking your Chase points and transferring them to Hyatt, but making sure you have enough to book with Virgin.

So the question that I’m asking myself is, “Right now there is this bonus to Virgin. Do I think it’s a good idea to speculatively transfer points now so that when you do want to book the tickets later, you have them?” There’s a possibility in the world that five months from now, you don’t end up actually wanting to go to Japan and then you have a bunch of Virgin points lying around.

I talk to clients about this stuff all the time. Like what if you transfer the points and then in the interim, the flight that you want to take disappears because someone else booked it, you have to be OK with having all those points locked in a particular airline. So that’s my question to you. I mean, we could wait, in which case, you should not necessarily book hotels yet because you don’t exactly know how many points you’re going to have in the end to do so. Or you could transfer points now, lock in this 30 percent bonus, and just plan, hope, whatever, that nothing changes between now and September, October.

Aislyn: Well, I’m curious to know what you would do, but right now, I mean, we were supposed to take this trip back in 2019, 2020. And of course, pandemic shut that down. So, and I’ve already requested my sabbatical time off. My partner’s requested time off. So we’re pretty locked in to making this happen. Like it would take an act of God. So I feel like we’re probably relatively good candidates for this, but what would you do if it were your situation?

Brian: Let’s see, let me do some quick math because what we’re talking about here—you’re flying from the West Coast. Uh, I have to do a quick search here: Virgin Atlantic, ANA, award chart. Because the West Coast to Japan is actually cheaper than East Coast to Japan.

Let’s see. Yeah, I was just looking at this yesterday for a client. OK, here we go. So western U.S. to Japan would be only 90,000 points round trip using Virgin Atlantic miles. So let’s say that’s 180,000 for the two of you, divided by 1.3. That’s 139,000 Chase points you’d have to transfer today with their current bonus. Which means you’d be left with like 180ish thousand Chase points left, right? I, if I had that number of Chase points, I’d probably do it to be honest.

And just so we’re clear what that would mean also for your return flight. You can’t book your return flight until like one to two weeks in advance either. So likely that means you’re going to be in Japan, like, and you have to get the ticket home when you’re in Japan. Does that make sense?

Aislyn: Yeah, it does. I mean, this is how I was envisioning this trip, so I feel like, yeah, let’s do it.

Brian: OK. So if you want, I do actually have a set of instructions I could send to you about how to transfer Chase points.

Aislyn: Sure, that would be great.

Brian: They’re fairly straightforward because Chase does want to make it easy for you. And then you’ll have your 180,000 points waiting in Virgin Atlantic. What I can do in the meantime, I can actually set some alerts for myself because you never know, maybe a flight does become available. And then, you know, we can text if that does happen, because this is, you know, five months from now, it’s possible between San Francisco and Tokyo, something will open up, uh, or from L.A. to Tokyo or whatever, you know, you said you were flexible. So if that’s the case, I can just get in touch with you and say. “Hey, do you want to book this today?”

Aislyn: Yeah, great. I love it. Let’s do it. So I’ll move the points over today and then we’ll just go from there. And then I’ll decide in the meantime, if I want to buy a refundable cash ticket.

Brian: Yes. Yeah. That’s the question. Um, you know, it’s funny if it were me, like, two years ago, I probably would. Nowadays—my God, my wife will love that I’m saying this out loud—I wouldn’t, I would just trust that we’d find something to fly where we want to go. She’s a last-minute planner, and that’s partially why we did the honeymoon last minute. I don’t like doing it that way, but if it means you get a really good deal and you’re willing to just plan things as you go, fine.

Aislyn: How often do you have people actually say that they’ll do this—they’re willing to kind of leave things till the last minute?

Brian: I have a couple of clients who consistently do that. I have a guy who contacted me today and said, “Can you get me flights to Hong Kong on May 6th?” [I said] like, “I’ll look, you know, I can’t guarantee anything, but I’ll look.” I’m sorry, it was May 11th. I told him I had to wait until probably May 6th to find something because five days in advance is a sweet spot for where he wants to go.

But most of the time people need some convincing. And to be quite honest, two years ago, when I bought this business, I needed some convincing that that was true, also. The former owner told me all the time he would tell people, “You got to wait until a week in advance, wait until a week in advance.” And, you know, his clients would be like chomping at their nails thinking this isn’t going to happen. And that’s kind of what I felt at first, even though I had read reports, I had him to trust. But now I have so much experience doing it that, like I said, like 95 percent certain you’ll find something to book using those Virgin Atlantic miles.

Aislyn: It sounds like maybe there might be flexibility in where in Japan you land. Like it might not necessarily be SFO to Tokyo. Is that part of the, the flexibility is where you actually end up?

Brian: I think it will actually be SFO to Tokyo. I realized after, when I said the Osaka route, that is on United specifically, and they don’t have the same deal with Virgin Atlantic. So it’s gotta be on what we say, “ANA metal,” meaning the plane that you fly is an ANA plane, and it goes from San Francisco to Tokyo, not to Osaka, it does go L.A. to Tokyo. I think there’s a Seattle–Tokyo one. But sometimes they don’t fly that one all the time. So, but whatever’s available, I’ll be looking.

Aislyn: OK, I’m excited and I can’t wait to reveal how it all turns out in five months. Well, is there anything else that you want to add about what you do or this whole points and miles business?

Brian: My wife likes to say this: Anyone who’s making more than a high school math teacher as their income should be flying business class more often, because if I can do it, you can do it.

Aislyn: That’s a great note to end on. I love it. Thank you so much, Brian.

Brian: Awesome. Thank you too. This was fun.

Aislyn: So, yes. I am waiting until late September to book my flights. You should’ve seen my partner’s face when I told her that we were waiting one to two weeks before a trip to book. And yes, I also feel a little anxious. But I do have faith in what Brian said, his knowledge and the systems that all makes sense to me. And I am so relieved that I didn’t have to do anything other than transfer some points. And Brian made that process super easy too. So I am happy to be in his capable hands. And I think we probably will book a couple of economy tickets just as backup, but anyway.

I will share an update in an Unpacked episode once we book our tickets. So rest assured you’ll hear the end of the story. In the meantime, you can find more information about Award Magic on their website, award magic.com. In our show notes, I’ll link to that as well as the company’s social media handles. I’ll also link to the other award platforms that Brian mentioned. Happy travels.

Ready for more unpacking? Visit afar.com, and be sure to follow us on Instagram and Twitter. The magazine is @afarmedia. If you enjoyed today’s exploration, I hope you’ll come back for more great stories. Subscribing makes this easy! You can find Unpacked on Apple Podcasts, Spotify, or your favorite podcast platform. And be sure to rate and review the show. It helps other travelers find it. We also want to hear from you: Is there a travel dilemma, trend, or topic you’d like us to explore? Drop us a line at afar.com/feedback or email us at unpacked@afar.com.

This has been Unpacked, a production of AFAR Media. The podcast is produced by Aislyn Greene and Nikki Galteland. Music composition by Chris Colin.

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