S3, E17: The Experience of Using a Concierge Service to Book Award Flights

Using points and miles for travel can be tricky. Some find it exciting, while others may feel overwhelmed. This week on Unpacked, we delve into a service that takes care of the tough stuff for you, so you can focus on planning your dream trip.

Transcript

Aislyn Greene, host: Welcome to Unpacked, the podcast where we break down one complicated travel topic each week. This time, we’re taking a look at an easier way to use points and miles to book your travels.

This topic might sound familiar because last year, we aired an episode all about points and loyalty programs. I had a conversation with Paul Rubio, Dinogo’s expert on points and miles, about the best credit cards for earning points and maximizing their value. He offered some great tips that I’ve actually put into practice. A few months ago, I started planning a trip to Japan and hoped to use the Chase points I’ve accumulated. I did some research, got started, but quickly felt overwhelmed and wanted to quit. So I set it aside. Then, in our Where to Go This Summer episode, travel writer Mark Ellwood mentioned a service called Award Magic that he pays to handle all his points booking.

I reached out to Brian Cohen, the owner and CEO, who explained how he got started in the business, how his services operate, and, to my surprise, agreed to assist me in booking my Japan tickets in an unexpected way.

Brian, it’s a pleasure to have you on Unpacked today. Welcome!

Brian Cohen: Thanks for having me.

Aislyn: Your business name, Award Magic, is fantastic. Can you share what it’s all about and what exactly you do?

Brian: Of course. I like to think of Award Magic as the ultimate way to help you earn and redeem credit card points for travel. Whether you’re booking standard economy seats or, if you want to splurge a bit, securing business class tickets for less than the price of an economy fare, that’s what we specialize in.

Aislyn: I’m loving this! And I’m definitely excited to dive deeper into it soon, but before we do, I’m curious—how did you end up in this line of work? Were you always someone who was passionate about points and miles and maximizing their value?

Brian: Well, I am now, for sure. But when I first stumbled into this, I was pretty hesitant. It all started when I was having lunch with some friends, and a new guy sits down next to me and casually mentions he has 46 credit cards. I was immediately intrigued and had to ask, ‘What’s that about? I need to hear more.’

He replied, ‘It’s Shabbat, so I’m not discussing it now, but let’s grab drinks later.’ So, we did—several times. This was back in early 2014. By the time he finished explaining it all, I was hooked. I started reading blogs, visiting websites daily, signing up for credit cards—just a few weeks ago I got my 39th card in this period. Over the last decade, I’ve had close to 90 or 100 credit cards.

I’m fascinated by learning how to maximize these cards, staying updated with all the changes, and applying it all. I’ve been helping friends and family out since then. Through this, I’ve managed to fly business or first class to places like Australia, Singapore, Japan, the Maldives, and South Africa. My wife and I even went on our honeymoon to Japan using miles! We really enjoy traveling.

Aislyn: That’s incredible! It sounds like you’re really the perfect person for this.

Brian: At the time, I was a high school math teacher, teaching for 14 years. I’ve always had a knack for figuring out rules and finding ways to explain them clearly to others. And I’ve also enjoyed finding ways to work around those rules. I always thought I’d make a good accountant if I ever tried—so now, I guess this is my version of that. I’m essentially managing points the way an accountant manages finances. That’s my take on it.

Aislyn: How did you go from helping just friends and family to offering your services to others?

Brian: It was all about timing. I was wrapping up my time as a teacher, moving from Brooklyn to Baltimore, and was looking for something new. Teaching during the height of COVID wasn’t much fun, especially in New York. I needed a break from the classroom. Then, a friend of a friend happened to be selling his company, which he’d started back in 2011.

It felt like the perfect moment to dive into something different. I bought the company and got an amazing deal—of course, it was a great deal. Everything he said would happen has come to pass, and then some. I’ve been working on growing the business, including exploring opportunities in the honeymoon industry and offering round-the-world tickets, which is something we can talk about too. It’s been a lot of fun.

Aislyn: That’s such a great story. You’ve got a really interesting reason for wanting to get into the honeymoon business. Would you mind sharing your personal experience with that?

Brian: I got married in May 2023, so we’re almost at our one-year anniversary. As I was preparing for the wedding, I had a lot of discussions with my wife about the business I had acquired—thanks to her input and support, I should add. Together with our parents, we worked out a strategy: which credit cards should we sign up for to pay for parts of the wedding, allowing us to rack up points for future travel?

For example, my mother-in-law covered most of the hotel costs during our stay. I got her to sign up for the Marriott credit card, as we were staying at a Marriott hotel. Now, she has accumulated hundreds of thousands of points, enough to stay at Marriott hotels for free for the next several years—thanks to our wedding.

Aislyn: That’s amazing! So how long did you get to spend on your honeymoon with all those points?

Brian: We spent seven weeks traveling to 10 countries. Since we had a short engagement—we got married in May and got engaged the previous November—we didn’t plan much ahead. By the time we left the U.S., we had tickets to Japan, a return flight from Frankfurt, and five nights booked in Tokyo. But the rest of the trip was spontaneous. We’d decide where to go next, figure out what points we had available, and find the best deals to use them. And that’s where my magic came in, I suppose.

Aislyn: That sounds like a dream! I’d love to learn more about the work you do. As someone who isn’t keen on spending all my time studying points, miles, and credit cards, I was so relieved to hear about your services. You came highly recommended by one of our travel writers. Can you tell me more about what you offer and how it works?

Brian: I like to divide my services into two areas: earning and spending. On the earning side, I host workshops about once a month. I offer a beginner’s workshop for those just starting out, with the next one scheduled for the end of May. I also hold an intermediate-level session for people who are already familiar with the basics but want to learn more about the tools and strategies we use to help book travel.

Additionally, I offer one-on-one or small group consultations. If you want to learn how to make the most of the credit cards you currently have, or if you’re thinking about switching cards, I’m happy to help. There’s a whole world of options when it comes to earning points, and I’m here to guide you through it.

On the spending side, if you’d prefer not to spend the time yourself and you’ve accumulated a large number of points—say, 400,000 Chase points or 300,000 American Airlines miles—and you want to use them for travel, you can reach out to us. Let’s say you’re in Chicago and want to fly to Venice, or you’re in Miami and dream of going to Singapore. We’ll help you figure out if you can book those flights in business class using your points.

My team and I will dive in, run searches with various tools, and analyze the best options for you. Sometimes we work directly with airlines, but we also have access to specialized search tools that have emerged in recent years. We’ll present you with the best choices, and then you can select the ones you prefer. With your approval, we’ll then book the flights for you, so you don’t have to deal with the hassle. Our goal is to help you maximize your points while minimizing the effort on your part, ensuring you get to your destination stress-free.

Aislyn: That sounds amazing! Could you walk me through your pricing structure? How much do you charge for a workshop, or for a consultation like this one?

Brian: Of course! A class usually costs between $30 and $40 for an hour-long session. I keep the group size small—no more than 20 people, sometimes 25, depending on the day—so everyone has the opportunity to ask questions towards the end. For one-on-one consultations, prices range from $150 to $350, depending on the type of consultation, and everything is listed on my website.

On the spending side, if you prefer to work with my team over email, there’s a $40 search fee. For a standard round-trip flight we help book, the cost is $225 per person. The search fee is deducted from your final total, so if you're booking for two people, the full charge would be $450, with the $40 paid upfront.

For those seeking quicker service, I offer AM First Class. This guarantees you’ll work directly with me. I’ll reach out via phone, text, email—whatever you prefer, though I won't overwhelm you if you’d rather not be contacted frequently. This service has a higher price point: a one-time $100 registration fee, and each round-trip flight booked thereafter costs around $325 per person.

Aislyn: What if someone isn’t happy with the flight options available, even after going through this process? How do you handle that situation?

Brian: For the standard tier, the $40 search fee is non-refundable. It’s essentially a deposit to confirm that you want to engage with my services. If we don’t find any flights that meet your needs, that’s the only cost you’ll incur. If you do find a flight you like, the remaining balance will be due.

For AM First Class, anyone who wants direct access to me pays a one-time $100 registration fee. After that, they can tell me where they want to go, and I’ll do a search for them whenever they need it—no additional cost for the search itself. However, when it comes time to book, the cost will be higher. That’s the trade-off.

Aislyn: Understood. How have people responded to your services? What do they typically want when they come to you?

Brian: Most people I talk to have never heard of this kind of service before, and their reactions are typically, 'Oh wow, that’s amazing! Can you help me get to Iceland next week?' For those who are familiar with points and miles, they tend to say, 'I’ve heard of that before' or 'I’ve tried a few things myself, but I’m stuck—can you help with the tricky parts?' Often, they reach out a few months later after struggling with a destination, like, 'I’ve been trying to book a trip to Japan, but I can’t make it work—can you help?' And I do my best to assist.

Aislyn: Wow, that’s incredible. What would you say is the biggest challenge people face when it comes to points and miles—or maybe even multiple challenges?

Brian: The biggest challenge is probably the devaluation of points over time and the limitation of award ticket availability. When you use points to book a flight, that’s considered an award ticket. Years ago, it was much easier to find available award seats because airlines were eager to offer them. But as more miles are distributed, it’s become more difficult to find available seats, leading to tighter restrictions on award bookings.

These days, there are fewer award seats available, so you need to be on the lookout for when they’re released and know the best way to use your points to book them. The good news is, it’s possible to earn more points than ever before. The credit card I just signed up for had a 250,000-point bonus, which was the largest I’ve ever seen. And just three days after I got approved, they increased it to 300,000 points. So, you could say it’s a bit like inflation—or devaluation, I’m not sure—but I’m certainly happy to take advantage of the points.

Aislyn: Wow, that’s crazy.

Brian: Yeah, it's like inflation or devaluation in real time! But honestly, I wanted those points, so I signed up for it.

Aislyn: Got it. What card is that?

Brian: It’s the American Express Business Platinum card. The interesting part is that Amex runs targeted offers, meaning you might get one, or you might not. I spent three weeks trying from four different browsers in private mode, and every time I visited their site, I was only offered a 190,000-point bonus.

I knew there had to be a bigger bonus out there, and it wasn’t until my wife and I were sitting in the American Express Centurion Lounge at Philadelphia International Airport that I finally found it. I opened my laptop, logged onto their Wi-Fi, and boom—the offer appeared right there.

Aislyn: So the secret is, you just have to be in an Amex lounge? That’s amazing. Well, we’ll dive into this more when we discuss my situation, but can you walk me through how the process works when someone wants your help to book a ticket or asks you or your team to take care of it for them?

Brian: It’s pretty simple, really. You just reach out through our website’s form, or if you’d prefer, you can book a time to chat with me about how our services work. After you submit the form, we’ll do a quick intake to make sure we’ve understood your request clearly. Sometimes people make small errors when typing, so we double-check all the details.

Once that’s done, my team assigns someone to work with the client, and they start exchanging emails, booking flights, and so on. If it’s me personally, I’ll typically follow up with an email letting you know when I’m available—usually the next day—and I’ll give you some options to consider. After that, we go back and forth until you either decide, "None of these options work," and we part ways, or you say, "Yes, book option one for the outbound and option three for the inbound," and we proceed.

If you’re ready to book, we send you a set of instructions, which can be as simple as, "Please provide your Alaska Airlines login details, and we’ll handle the booking from there."

Typically, people have what’s known as transferable currencies—like Amex Membership Rewards points or Chase Ultimate Rewards points. We guide them through the process of transferring those points so they don’t get lost along the way.

Aislyn: Where do you see your business going in the future, especially considering it’s still relatively new to you? What are your goals moving forward?

Brian: That’s an interesting question. I never really thought much about work-life balance before. As a teacher, it was something I had no choice but to accept. But now, as a small business owner, I get to set my own pace. And I truly enjoy helping people book flights, so I think I’ll continue focusing on that. I’m particularly interested in offering flights for things like quick trips between New York and places like—Serbia, for example.

I also really enjoy helping people book round-the-world tickets. There’s a special deal with All Nippon Airways, based in Japan, where you can use around 145,000 points for up to 12 business-class flights across the globe. A typical business-class ticket to Europe alone can cost 70,000 points, so this deal is incredible. Every time I help someone book this, they’re thrilled. It’s one of my favorite parts of what I do.

I’m also hoping to carve out a niche by helping couples plan their honeymoons. If I can assist them in choosing the right credit cards to earn points and then use those points for round-the-world tickets, that would be amazing. I’d love for that to become the core of my business.

Aislyn: I’m excited to see how it all develops. I’m curious, though—services like Point.me exist, and I was wondering how you think you compare to something like that. Do you view your services as different?

Brian: Some of those services are similar to what I do. Point.me, for example, offers its own concierge service where someone helps you book award tickets, so there’s definitely overlap. That said, I think there’s plenty of space in the market for all of us. Honestly, when I tell people about my services, 80% of the time they say, 'I had no idea something like that existed.' So, there’s still a lot of potential out there.

As for Point.me, I think most of their revenue comes from their search engine, which I’ve tried. I’m just not a big fan because the searches take too long, and since I’m doing searches all day, I can’t afford to waste that much time. But for people who want to do it themselves, I say, 'Go ahead and check out Point.me.' In my workshops, I also talk about other services like AwardLogic, PointsYeah, and Seats.aero, where I explain their strengths and weaknesses. If you want to dive into that world, fine. But if you’d rather not, you can come to me, and I’ll handle the details for you without the hassle.

Aislyn: Well, that sets me up perfectly to share my dilemma. I’m not sure if it’s a good strategy, but my partner and I have been saving up our Chase points—we’ve got the Chase Sapphire and Freedom cards—and we’ve been hoarding those points for a couple of years. I just checked today and we have 312,779 Chase points, 6,620 Hyatt points, and 38,531 Marriott points.

Our plan is to go to Japan this fall. I’ve actually earned a six-week sabbatical since I’ve been at my job for 10 years, and I want to spend most of that time in Japan. Ideally, I’d love to fly us both business class there and back. I was hoping to use the Chase points for the flights, and then possibly use the hotel points for accommodations. What would you recommend I do?

Brian: This is actually a great dilemma to have. We get a lot of people coming to us saying, 'I want to go to Japan.' It’s such a sought-after destination, especially since during COVID, Japan had a much longer lockdown than many other places. That created a lot of pent-up demand. I can totally relate—I had two tickets to Japan before COVID, but both got canceled. So when my wife and I went for our honeymoon, I was extra excited to finally get there.

I need to be upfront, though: Getting award tickets to Japan is tricky. If you’re okay with flying economy, it’s somewhat easier, though you might have to take a detour or two on the way. Some people even need to fly through Europe, which adds a lot of extra travel time. If you want to get to Japan on points, you basically have three options: You can book your ticket up to a year in advance, ideally 355 to 360 days out depending on the program; you can book last minute, a week or two before your flight; or, you can simply get really lucky.

Aislyn: Oh no, that sounds stressful!

Brian: Let me share our story with you to show how this all fits into your situation.

Aislyn: Sounds good. I’m all ears.

Brian: We knew Japan was our destination, and I told my fiancée at the time, 'Let’s not stress about booking these tickets too far ahead. We’ll just take it as it comes.' There are so many flights from major cities in the U.S.—New York, Boston, Dulles, Seattle, San Francisco—that I was confident we’d find business class seats at least a week or two before departure. It's pretty consistent.

We got lucky. Three weeks before we were set to leave, I spotted two flights with Japan Airlines departing from Seattle. I thought, 'Let me grab those.' And I did, which took all the stress off, but that was definitely a stroke of luck.

Now, in your case, you might not be able to do exactly what we did, since we had American and Alaska miles. You don't have those. The main U.S.-Japan airlines are Japan Airlines (JAL) and All Nippon Airways (ANA). For JAL, you can use any points within the OneWorld Alliance, with American being the top choice, which is what I used. You could also use Alaska miles, or even British Airways miles from your Chase points, as Chase transfers to British Airways on a 1:1 basis.

Aislyn: Got it, that makes sense.

Brian: For ANA, since they’re part of the Star Alliance, you’d need miles from any of the Star Alliance members, like United, Singapore Airlines, or Air Canada. But here's the twist with ANA: They have a unique partnership with Virgin Atlantic. Sounds odd, right? But you can use Virgin Atlantic miles to book ANA flights, as long as there's availability. And that's the key.

When I'm trying to book these flights, it might sound a bit complicated, but here’s my process: I start on the United website, looking for flights from the U.S. to Tokyo, since United lists ANA flights. If I spot an ANA flight, I’ll advise my client, 'Let’s transfer your points to Virgin Atlantic, and call them directly to book. You won’t be able to do it online, but if you reference the flight we found on the United site, they should be able to book it for about half the miles.'

Aislyn: Wait, really?

Brian: Yeah, here's how it breaks down. You mentioned you have around 312,000 Chase points. To book an ANA flight with United miles, it would be 110,000 miles per person one-way in business class, so you won’t have enough for that.

Aislyn: Alright.

Brian: But if you transferred those points to Air Canada (also an option through Chase), it would cost around 75,000 miles. You’d have enough for that. However, why burn through those points? With Virgin Atlantic, it’s only 50,000 points one-way. So you’re looking at a massive saving—going from 110,000 miles per person down to just 50,000. If you book for both you and your partner, that’s 200,000 points round-trip. You’d still have 112,000 points left, which I’d suggest using at a Hyatt hotel in Tokyo. That’s what we did.

Aislyn: Alright, let’s go for it! How long does it typically take to finalize bookings? What’s the usual timeline for this process?

Brian: If someone is ready to book, like it sounds you might be, it could take just a day or two. I had a booking request on Monday for a trip to Italy, and I wrapped it up today. But if someone is more particular—wanting to fly a specific airline on a specific day—it might take a few weeks. At that point, we’ll tell them, 'We’re running out of time, and we’re not a limitless service. If you’re not happy with the options we’ve provided, you may need to pass.'

Sometimes, especially with destinations like Japan, if someone is trying to book seven months in advance, which isn’t exactly a year or just a week, it’s unlikely we’ll be able to find their perfect flight.

For example, I once booked a trip for a client and his son flying from JFK to Zurich and then to Tokyo using Air Canada miles. They flew Swiss Air as part of a partnership deal. They were happy with it, even though they would have preferred a direct New York-Tokyo flight, but that just wasn’t available.

Aislyn: Got it.

Brian: Sometimes that happens. And for you, if you’re open to waiting until the last minute, I’m pretty confident—95 percent sure—that we can secure tickets for you using Virgin Atlantic miles. There’s always a bit of uncertainty, but some people aren’t comfortable with that, and they end up having to use more points or take a route through Europe instead.

Aislyn: Hmm, that’s a tough one. Part of me thinks, 'Yeah, let’s hold out for the best option.' But then I wonder, 'What if that 5 percent chance doesn’t work out? What happens then?'

Brian: I’ve been in a similar spot before. There was this one time I was heading to Australia. I had Qantas first class for the outbound, but couldn’t find anything for the return flight. Australia can be tough to book, especially because they don’t release many award seats in advance. But, if you're booking just a week or two ahead, it’s much easier to get a seat. I set up an alert for myself, and the moment I landed in Brisbane, I got a notification on my phone: two Qantas business class seats for the return leg. By the time I got off the train, those seats were booked.

Brian: Good question! I once booked a round-the-world trip for three guys from Reno. I think they’re in Japan now. When I booked it, I told them the same thing I told you: I was 95 percent sure it would work, but I had to book them on ANA economy for the return. The way the round-the-world ticket works, they could upgrade those tickets for free, so I told them I’d start checking for upgrades two weeks before departure.

Brian: No kidding, the very first day I checked, I found an upgrade. I messaged them when they were in Osaka and asked if the flight looked good to them. They gave me the green light, and within half an hour, they were upgraded to ANA business class for the flight home. They’ll be flying to L.A. in a few days, and I’m sure they’ll be thrilled with that experience.

Aislyn: That sounds great! So, if I decided to wait a week or two, would you book economy tickets first and then try to get upgrades? Is that how it usually works?

Brian: That was a strategy I used specifically for the round-the-world ticket. In your case, I might suggest booking a refundable cash ticket. This way, you’ve got something locked in, but if business class doesn’t open up, you can still cancel the ticket. It gives you some flexibility.

Brian: You can either pay for a fully refundable ticket, which might be more expensive, but you’d get your money back if you change your mind. Or, you could opt for a less costly refundable ticket and pay a cancellation fee—usually about $100 per person. It’s a bit of a trade-off, but it guarantees that you can get into business class if the upgrade becomes available. I’ve done this for clients before: they book a ticket, I check for upgrades, and then we cancel and rebook when a better flight comes up.

Aislyn: OK, that sounds like a solid plan. I’d love to see what options are out there now and then consider waiting, if that works for you.

Brian: Can you remind me of the dates you were looking at? And I’m pretty sure you’re on the West Coast—am I right?

Aislyn: We’re based in San Francisco, or more specifically the Bay Area. We usually fly out of SFO, but we’re open to departing from LAX or Seattle if needed. Our time off is from around October 5th to October 27th, give or take.

Brian: Got it. Let me do a quick search on the United site here.

Aislyn: Sounds good.

Brian: As expected, the flights are coming in at 200,000 miles or more each.

Aislyn: Oh my God.

Brian: To make my point clearer, let’s look at what’s available for May [2024]. Let’s see what we can find.

Aislyn: OK, sounds good. This is exciting.

Brian: Alright, here’s something. You could fly business class from San Francisco to Osaka. What day is that? Oh, it’s the 3rd—Friday. There’s also a flight from San Francisco to Narita that day. And, actually, ANA has some planes with their new business-class seat called ‘The Room,’ which is a huge upgrade. Business class has really evolved—it’s almost like first class used to be, and now first class is practically like a living room in the sky, which is unbelievable if you can snag that.

Brian: And the best part? Right now, there’s a 30% bonus on points transfers to Virgin Atlantic from Chase, American Express, and Capital One. So the 50,000 points I mentioned earlier? Take about a third off that number. For a flight that would typically cost $7,000, you’d only pay about 38,000 points.

Aislyn: That’s incredible.

Brian: To summarize, after running a search from San Francisco to Tokyo, I found that October flights are quite expensive. However, if you look at the next couple of weeks, you’ll see that there are plenty of business class seats available between San Francisco and Tokyo.

Brian: I did something similar this morning with a client. I told them, ‘You’ll need to transfer these points. Send me your login info, and I’ll take care of it.’ Or, in your case, I’d need to call on your behalf.

Brian: With Virgin Atlantic, because of our voices (yours being a stereotypical female voice and mine a stereotypical male one), I’d need to call with you on the line to authorize me to book for you. Once you give the green light, you can hang up, and I’ll finish up the booking. I usually call first to avoid the 15-minute hold times, then I do a three-way call with you to get the authorization before handling the rest.

Aislyn: Okay, so if I wanted to use Virgin Atlantic points, would a flight still cost 50,000 points per person per flight, or is that only the case if I wait until one to two weeks before departure?

Brian: That pricing applies to booking one to two weeks in advance—or 350 days ahead. But there's a caveat: airlines release award tickets in different fare codes. United, for example, has its own set of fare codes, like YN or ZN. These codes indicate that the tickets can only be booked using their points, and they tend to be more expensive.

This isn’t considered the Saver Award level. For business class at the Saver Award level, you're typically looking for an 'I' or 'J' code. So, as I check the availability for May 3rd on their site, I can see codes like 'United business I' and 'ANA business I.' That tells me if it’s in the Saver category, both Air Canada and Virgin Atlantic can also book that same seat because it’s now available to all partners at the Saver rate. Does that make sense?

Brian: Exactly.

Aislyn: OK. Looks like we’ll be waiting then.

Brian: Since you have Chase points, you can transfer them to United, but it’s going to cost 200,000 points for one of you to fly business class one-way. That’s definitely not worth it.

Aislyn: Absolutely not worth it. Alright, I think we’re going to wait and see. It's a bit exciting but also nerve-wracking. So, it seems like we’ll touch base around mid-September. Also, if I want to use my points for hotels, how should I balance that out to save as many Chase points as possible?

Brian: That’s a great question. So, between May and October, I’ve been thinking of a few options. Right now, transferring Chase points to Hyatt seems like one of the best moves for hotels, especially since it takes so few points. For instance, every February, my wife and I head to Cancun for her birthday and stay at an all-inclusive resort. We can book it for just 23,000 points a night for both of us, while the cash price would be $700 per night. It’s such a steal.

When we were in Tokyo, we stayed at the Hyatt Centric Ginza, which I think was 25,000 Hyatt points a night. So, for your situation, I’d recommend transferring your Chase points to Hyatt, but make sure you still have enough left for booking Virgin flights.

What I’m trying to figure out is whether it's a good idea to transfer points now, especially since there’s a bonus with Virgin Atlantic. If you transfer now, you'll be ready when you’re ready to book. But there’s a risk—what if in five months, you decide not to go to Japan? Or what if you don’t end up needing all those Virgin points? It’s a gamble.

I talk to clients about this all the time. For example, what if you transfer the points now, but then in the meantime, the flight you want to book gets snapped up? It’s important to be comfortable with locking your points into one airline. So here’s the dilemma: We could wait and not book hotels yet because you won’t know exactly how many points you’ll have. Or, you could transfer points now, lock in that 30 percent bonus, and just hope nothing changes between now and your travel dates.

Aislyn: I’m really curious what you would do in this case, but I can tell you, we were supposed to take this trip back in 2019 or 2020, and then of course the pandemic hit. I’ve already requested my sabbatical, my partner’s got his time off too, so we’re pretty much locked in. It would take something major for us to change our plans, so I feel like we’re pretty good candidates for moving forward. But if it were your situation, what would you do?

Brian: Let me do a quick calculation for you. Since you’re flying from the West Coast, I need to check Virgin Atlantic’s ANA award chart. Flying from the West Coast to Japan is actually cheaper than from the East Coast.

Okay, I was just reviewing this for a client yesterday. So, flying from the western U.S. to Japan will cost you only 90,000 miles round trip with Virgin Atlantic. That means for the two of you, it would be 180,000 miles total. With the current bonus, if you transfer 1.3 times that in Chase points, you’d only need 139,000 Chase points. After that, you’d still have about 180,000 Chase points left. Honestly, if I had that many points, I’d go for it.

And just to clarify, the return flight won’t be bookable until one to two weeks before departure. This means you’ll likely be in Japan first, and then you’ll need to book your return ticket while you’re there. Does that make sense?

Aislyn: Yes, that makes sense. This is exactly how I was imagining the trip, so I’m on board. Let’s move forward with it.

Brian: Great. If you’d like, I can send you a set of instructions on how to transfer your Chase points.

Aislyn: That sounds perfect, I'd appreciate it.

Brian: It’s pretty simple since Chase aims to make the process as easy as possible. Once you transfer the points, you'll have your 180,000 ready in Virgin Atlantic. In the meantime, I can set up alerts for myself. You never know, a flight might open up unexpectedly. We could check in a few months, and if something comes up between San Francisco and Tokyo, or from L.A., or wherever you’re flexible with, I’ll just reach out to you and say, 'Hey, do you want to book this?' and we’ll take it from there.

Aislyn: Sounds awesome! I’ll go ahead and move the points today, and we can just go from there. I’ll think about whether I want to get a refundable cash ticket in the meantime.

Brian: Yeah, that’s the big question. Honestly, if it were me a couple of years ago, I probably would’ve bought a refundable ticket. But now... well, my wife will probably laugh hearing this... I wouldn’t bother. I’d just trust we’d find a flight that works. She’s a last-minute planner, which is why our honeymoon was so spontaneous. I’m not crazy about that approach, but if it means you get a great deal and you’re okay planning on the fly, I’m fine with it.

Aislyn: How often do people actually go for the last-minute option? Is it something a lot of folks are willing to do?

Brian: I have a few clients who always book last-minute like this. One reached out today asking, 'Can you find me flights to Hong Kong for May 6th?' I told him, 'I’ll check, but no promises.' Actually, it was for May 11th. I told him that I’d likely need to wait until about May 6th to find something, since flying just five days out is often the best bet for that route.

Most people need some convincing, though. Honestly, when I first took over this business two years ago, I was skeptical too. The previous owner would always tell clients, 'Wait until a week before the flight.' Clients would be so anxious, thinking it wouldn’t work out. I felt that way initially too, even though I had read about it. But now, after doing it so many times, I’m about 95 percent confident that we’ll find something using those Virgin Atlantic miles.

Aislyn: It sounds like there might be some flexibility in your destination within Japan, like it doesn't have to be a direct flight from SFO to Tokyo. Is that part of the flexibility—where you land?

Brian: I think we’re sticking with SFO to Tokyo after all. I realized when I mentioned the Osaka route that it's specific to United, and they don’t have the same arrangement with Virgin Atlantic. So, it’s got to be on an ANA plane—meaning it’ll be an ANA flight from San Francisco to Tokyo. United does fly L.A. to Tokyo, and there’s even a Seattle to Tokyo route, though it’s not always available. I’ll be keeping an eye out for the best option, whatever comes up.

Aislyn: I’m so excited and can’t wait to see how it all pans out in five months. Is there anything else you want to share about what you do or the whole points and miles process?

Brian: My wife often says, 'Anyone earning more than a high school math teacher should be flying business class more frequently. If I can do it, so can you.'

Aislyn: What a perfect way to end! I love it. Thanks so much, Brian.

Brian: You're welcome! This was great. Thanks for having me.

Aislyn: Yes, I’m holding off until late September to book our flights. You should’ve seen my partner’s face when I told her we’re waiting until one to two weeks before the trip. I’m a little anxious too, but I trust what Brian said. His expertise and the whole system make sense to me. I'm relieved I didn’t have to do more than transfer some points, and Brian made that process really simple. I’m happy to be in his hands. We’ll likely book a couple of economy tickets as a backup, though.

I’ll share an update in a future Unpacked episode once our tickets are booked. You’ll definitely hear the full story then! In the meantime, you can find more info about Award Magic on their website, award magic.com. I’ll link to that, as well as their social media, in the show notes, along with the other award platforms Brian mentioned. Safe travels!

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You’ve been listening to Unpacked, a production of Dinogo Media. Produced by Aislyn Greene and Nikki Galteland, with music by Chris Colin.

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