I'm going to be honest and say I don't have a lot of experience booking flights to Asia.
What I DO know is it's typically cheapest from the West Coast and award seats are in high demand, which means you really need to be booking a long ways out or get lucky last minute.
So when this challenge landed with locked-in Thanksgiving dates and a solo trip to Japan attached, I figured I'd drawn the short straw. 🤷♀️
Final tally: 192,000 points and $453 for six nights, split between Tokyo and Kyoto.
But here's the part I'd rather lead with than bury at the bottom: I found better flights AFTER I thought I was finished searching. Not a little better. 40,000 points better.
And the only thing it cost me was one more day of PTO. Lemme explain.
First, the ground rules
Quick refresher on the challenge: one traveler, the whole trip inside a fixed window over Thanksgiving week, 200,000 points and $2,000 to work with, and all the points have to come from a maximum of three credit cards.
I used two. My Chase Sapphire Reserve® for Hyatt stays (of course), and my American Express® Gold Card, for the 30% transfer bonus to Avios.
Here's the itinerary:
Nov 23: Dallas (DFW) → Tokyo, American Airlines flight booked through Qatar (31,000 Avios)
Nov 24–26: Three nights in Tokyo (54,000 World of Hyatt points + $453)
Nov 27: Tokyo → Kyoto on the Tokaido Shinkansen
Nov 27–29: Three nights in Kyoto (90,000 World of Hyatt points)
Nov 30: Kyoto → Tokyo by train, then Tokyo → Dallas (31,000 Avios)
Yes, I moved my departure to a Monday. Again. At this point it's less of a strategy and more of a personality trait. 😏
Getting there: the flights I found on the second pass
There were some slightly better award prices from the Central Time Zone region, but they doubled or tripled the duration with layovers in LA, NYC, or even in Amsterdam. 💀
And if I've only got a week off for a trip, I'm not going to spend 38 hours getting there if I don't have to.
So, in this instance, I'd use AAdvantage Miles to book nonstop flights to and from Dallas to save time and avoid any potential travel day headaches. 👇
I again opted to shift my travel days forward to take advantage of better award fares, so these flights leave on November 22nd and return on the 29th.
At least in this instance, you could technically still make it to work the next day if you were based somewhere near Dallas. You just might be a little jetlagged. 🤷♀️
That version ran 88,000 miles round trip. Which I would have accepted, right up until I didn't have to.
Note: After my initial search above, I later found AA flights available through Qatar on Monday, Nov. 23rd and 30th for 31,000 Avios each. With the current 30% transfer bonus to British Airways, Iberia, and Aer Lingus from cards that earn MR points, I could transfer 48,000 points to book round-trip flights in economy if I take a day off work. As I've said, it pays to be flexible! 👇
So let's do the math on that, because it's the whole article.
88,000 miles for the original nonstops. 48,000 transferable points for the same carrier, one day later.
That's 40,000 points saved — enough to cover a fourth night in Kyoto — in exchange for a single vacation day.
Everything below assumes the shifted dates.
A tale of two cities
Having never been to Japan, I think I'd go the popular first-timer approach of fitting both Tokyo and Kyoto into one trip. It's a squeeze, but if I'm there by myself, I don't mind some faster-paced travel/sightseeing.
In a perfect world, you'd have time for a longer trip, but PTO gonna do what PTO gonna do. 🫠
The high-speed bullet train, the Tokaido Shinkansen, connects the two cities in roughly 2 and a half hours, and I don't mind the opportunity to read on the train and relax mid-vacay if it lets me experience more.
My flight arrives in the evening, so I'd start my stay in Tokyo, just to ease into the trip after a long flight in economy.
And with the Qatar flights freeing up those 40,000 points, I'd have enough to cover 5 of my 6 hotel nights on points.
Three nights in Tokyo
I'd start in Tokyo at the Hyatt Regency, paying 27,000 points a night for a room with club access, meaning breakfast and snacks are included in my stay. 👇
I would pay for 2 nights with points and the final night with cash ($453) for a club access room. 👇
Keep in mind: 27,000 points against a $453 cash rate is about 1.68 cents per point, which is a perfectly good redemption. I paid cash on night three because I was out of points by then, not because the points were a bad deal.
That's what a 200,000-point ceiling does to you. Sometimes the right answer is the one you can still afford. 🤷♀️
Three nights in Kyoto
I'd then pack up and head to Kyoto for 3 nights, staying at the Hyatt Regency in Kyoto for 30,000 points a night. It's a slightly older hotel but widely reviewed as a nice stay. 👇
And as it's slated to close next year, I'd take advantage of the stay while it's still an option.
Hotels in Kyoto were a lot more expensive and there was less availability for the dates that I was searching, so I would opt to pay for my 3 nights here with points.
90,000 points for three nights in the most in-demand city on the itinerary, during the most in-demand week of the year. I'll take it.
Getting home
Because my flight leaves in the evening, I'd feel comfortable checking out in Kyoto and making my way back to Tokyo via the bullet train to catch my flight.
The return is just the back half of that same Avios booking, so there's no second search and no second transfer to worry about.
Tip: build in more buffer than you think you need on that last day. Two and a half hours on the train is the easy part. Getting from the Tokyo station to the airport on the far side of it is the part that'll get you.
The damage
Adding it all up:
Points: 48,000 (transferred for the Avios flights) + 54,000 (Tokyo, 2 nights) + 90,000 (Kyoto, 3 nights) = 192,000
Cash: $453 (third night in Tokyo) + bullet train tickets + taxes and fees
That leaves 8,000 points on the table and plenty of the $2,000 left over to cover taxes, fees, and my train tickets.
Which, after reading what everybody else on the team spent this week, feels almost rude. 😏
What I'd actually do (if I weren't locked into these dates)
Stick with the original flights and eat the difference. If I didn't want to shift my flights and take a day off work and stayed with the AA flights I originally mentioned for 88k, I'd only have 112,000 points leftover to book hotels. In that case I'd probably keep my Kyoto stay the same and pick a cheaper option in Tokyo. I'd shift over to the Hyatt Regency Tokyo Bay, where I could pay 21,000 points for one night and $406 for the last two nights. Plus, I'd have access to the free shuttle to Tokyo Disneyland! 👇
Go through Avios instead of AA, every time. Booking directly with AA is a little more difficult because those points are difficult to come by. You'd need one of these co-branded cards or this one and then transfer points over to AA to book. This is another reason why I personally would likely need to move my dates to book the flights through Qatar. Avios are super easy to come by whereas AA are not.
Book a lot further out, or get lucky at the last minute. Award space to Japan is in high demand and there's not much middle ground. Thanksgiving week is the worst possible test of that.
Take more days. Six nights across Tokyo and Kyoto is doable solo. It is not relaxing. If you can stretch this to nine or ten, the Shinkansen day stops being a logistics problem and starts being part of the trip.
The bottom line
Can one person get to Japan and back over Thanksgiving week, plus six nights in two cities, on 192,000 points and $453?
Yes. And unlike some of the trips you'll read this week, I'd actually book this one. 😉
But the real takeaway isn't the hotels or the routing or any clever transfer trick.
It's that I did a full search, landed on an answer I was happy with, and then found something 40,000 points better by moving one day.
One. Day.
So if you're locked into your dates the way I was locked into these, poke at the edges anyway. Look at the Monday. Look at the Tuesday. Look at the same airline through somebody else's program.
And if Japan isn't on your list at all, that's okay too. Who knows where we'll end up next week! 🤷♀️
