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How I helped a points and miles beginner book a trip to Japan

June 01, 2020
19 min read
Kiyomizu-dera Temple
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Meet my friend Dan. I introduced him to the points and miles world last year after he discovered his love for travel on a quick solo trip to Munich and Vienna. He was hungry to travel more, but being a grad school student, he wanted to do it without breaking the bank.

Naturally, I got him started with a transferable points credit card and helped him maximize his everyday purchases using shopping portals and dining programs. Soon enough, Dan had accrued over 150,000 points and already had a destination in mind: Japan.

We decided to take the post-quarantine trip together and — naturally — pay for as much of the trip as we can with our collective balances of points and miles. After much discussion, our rough plan was to fly into Tokyo, spend a few days there and visit two other cities: Kyoto and Osaka. Both the cash and points costs of the trip will be split between the two of us.

I'll give you an inside look at how we're booking this trip from a beginner's perspective. You'll see how we booked the tickets and just how much is possible with a couple of travel rewards credit card welcome bonuses and everyday spending.

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Travel rewards credit cards to jumpstart the trip

Dan applied for his first points-earning credit card in late 2019. I recommended that he start with the Chase Sapphire Preferred Card; at that time, he was under 5/24 and putting all of his everyday spending on a (gasp!) Spirit Airlines cobranded credit card.

Plus, Dan is a foodie who frequently takes Lyfts around his hometown of Chicago. This made the Sapphire Preferred card perfect for him as the card earns 2x Chase Ultimate Rewards points per dollar spent on travel and 3x points on dining purchases, and 5x points per dollar spent on Lyft purchases.

(Photo by John Gribben for The Points Guy)

The card's current welcome bonus is 100,000 Chase Ultimate Rewards points after spending $4,000 on the card in the first three months after account opening. He quickly hit the card's minimum spending requirement through a mixture of everyday expenses, rent payments through Plastiq and various other purchases, giving him a nice head start towards our Japanese adventure.

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Dan also applied for a Chase Freedom Unlimited card to earn 1.5% cash back on all of his non-bonus spending. One of the card's best benefits, however, is being able to convert earned cash back to Chase Ultimate Rewards points so long as the cardmember also holds a Chase Sapphire Preferred Card, Chase Sapphire Reserve or Ink Business Preferred Credit Card.

At the time Dan applied, the card offered a $200 cash-back bonus after spending $500 on purchases (no longer available) in the first three months of account opening. Since Dan already holds a Chase Sapphire Preferred card, he transferred the $200 bonus to 20,000 Ultimate Rewards points after meeting the bonus.

Related: How to transfer Chase Ultimate Rewards points between accounts

Enter the American Express® Gold Card

A couple of months later, Dan asked me for recommendations on another credit card. He had a tuition payment coming up that he could pay with a credit card, so he could quickly earn a solid welcome bonus. We discussed a few different Chase options due to his sub-5/24 status, but in the end, he wanted a card that earned more than the Sapphire Preferred on dining and airfare.

One option we considered was the Chase Sapphire Reserve, as it earns 3x points per dollar spent on all travel and dining, but has a $550 annual fee. The fee is largely offset by an up to $300 travel credit, but Dan still wanted to look elsewhere.

Why? Unfortunately, you can't get the welcome bonus for a Sapphire Reserve Card if you already have a Sapphire Preferred Card.

Related: Sapphire showdown: Chase Sapphire Preferred vs. Chase Sapphire Reserve

After some discussion, Dan ended up applying for the American Express® Gold Card. Currently, the card offers a welcome bonus of 60,000 Membership Rewards® points after you spend $4,000 on eligible purchases with your new Card within the first 6 months of account opening. However, he was able to get an elevated welcome bonus by applying through my referral link.

Plus, the card has an excellent earning structure: He'll earn 4x points per dollar at restaurants and 4x points per dollar at U.S. supermarkets (up to $25,000 in purchases per calendar year, then 1x) and 3x points per dollar spent on airfare purchased directly with airlines or through Amex Travel. Plus, he'll have no problem eating through the $120 dining credit, (enrollment required).

Dan quickly met the spend requirement for his American Express Gold Card and has kept using the card for dining at restaurants and grocery purchases at U.S. supermarkets ever since. Likewise, he's continued to put all other travel expenses on his Sapphire Preferred and nonbonused spend on his Chase Freedom Unlimited, meaning that he's earning more than 1 point per dollar on all of his spending.

Introducing Dan to shopping portals and dining programs

Throughout this process, I also helped Dan get started with using shopping portals and dining programs to earn additional miles on everyday purchases. If you're new to the miles and points game, you can use shopping portals to earn extra points on online purchases so long as you click through the portal first.

There are a number of different shopping portals out there, but I recommended that Dan use the Rakuten and Chase Ultimate Rewards shopping portals whenever possible so he can consolidate his points. While Rakuten is traditionally seen as a cashback portal, you can opt to earn American Express Membership Rewards points at a rate of 1 point per $0.01 earned in cash back.

On the other hand, dining programs let you earn extra points when you dine at participating restaurants around the country. These points are earned in addition to the points earned with a credit card, and the number of points you'll earn varies by dining rewards program and your status in the dining program; you can earn what most dining programs call "VIP" status by dining a set number of times.

I recommended that Dan join a dining rewards with an airline or hotel group that's also a Chase Ultimate Rewards partner. In the end, Dan signed up for the IHG Rewards Club dining program and quickly made VIP status after 11 qualifying dines, meaning that he now earns 8 IHG Rewards points per dollar spent on purchases at participating restaurants.

Related: How to earn Chase Ultimate Rewards points

Planning the trip

As of last month, Dan had a total of 72,000 Amex Membership Rewards points and 120,000 Chase Ultimate Rewards points, most of which he planned to use for our tour of Japan. In addition, Dan earned roughly 5,000 IHG points through the IHG Rewards Club dining program — unfortunately, however, we didn't get to use these on our trip.

Dan and I originally wanted to take this trip in summer 2020, however, we decided to postpone the trip to early 2021 due to the global coronavirus outbreak. Since we're planning so far in advance, our schedules were pretty flexible, but we did have a trip length in mind: 10 days. This gives us four days in Tokyo, three in Kyoto and three in Osaka.

With these date parameters in mind, we began searching for an itinerary that worked for both of us. Our goal was to book an itinerary that we could split evenly in terms of both points and cash costs, but given my stash of points was a bit higher than Dan's, I offered to pick up some of the points slack if need be.

Related: The best ways to travel to Japan with points and miles

Booking flights to, from and around Japan

(Photo by Zach Griff/The Points Guy)
(Photo by Zach Griff/The Points Guy.)

Our flexibility ended up being super helpful as we planned our flights. When you're not tied to a specific set of dates, you can book whenever there's award space for your flight. Because of this, we started our search by looking for a specific airline and business-class product that we wanted to fly.

Dan left the flight planning to me, so I set out to find something that would really "wow" him as he's never flown international business class before. Additionally, I wanted to find something that was new to me as well — I've flown to Japan before in JAL and American Airlines business class, so I kept those off the list for this trip. Another thing I kept in mind when looking for a business-class product was Dan's point balances. Thankfully, Dan had a solid number of points available to him across the two most powerful transferable points programs, so we had plenty of options. However, I needed to stay cost-conscious as we also needed to book hotels with points.

Booking ANA business class with Virgin Atlantic Flying Club miles

In the end, I settled on booking ANA business class using Virgin Atlantic Flying Club miles. Not only is ANA's new business-class product excellent, booking through Virgin Atlantic is an excellent deal at only 95,000 miles round-trip from the Midwest and East Coast to Japan. Plus, Virgin Atlantic is a transfer partner of both Chase Ultimate Rewards and American Express Membership Rewards, so we can both book our flights using our respective stocks of transferable points.

Before we further discuss this booking though, I want to make something clear: we booked these tickets before Virgin Atlantic's current financial woes came to light. That said, I don't recommend transferring points to Virgin Atlantic to book ANA tickets until we're sure that Virgin Atlantic will make it through the coronavirus travel downtown; if you transfer now, there's a chance your ticket may not be honored if the airline goes insolvent and your miles could be rendered worthless if the airline enters bankruptcy.

With that out of the way, let's discuss our flight itinerary. Dan lives in Chicago and I live in New York City. As of writing this article, ANA's new business-class product only flies from New York-JFK to Tokyo (HND) while the Chicago route is still operated by an older plane. After some convincing though, I got Dan to agree to fly to New York City for the outbound flight so long as we returned directly to Chicago. This is possible because Virgin Atlantic does allow open-jaw tickets on ANA bookings.

After this, it was time to actually book our tickets. ANA award space isn't bookable on Virgin Atlantic's website, so I used to find award space. Finding the award space was simple: I just searched United's site for two nonstop, ANA-operated tickets with saver award space and took note of the dates and flight numbers. You can see an example of a bookable flight in the screenshot above.

After finding these flights, I sent Dan the flight numbers and had him call Virgin Atlantic Flying Club to put his flights on hold. At the same time, I also called Virgin Atlantic and had my tickets put on hold. Virgin Atlantic offered to put our tickets on hold for 48 hours, giving us more than enough time to transfer points.

I instructed Dan to transfer all 72,000 of his Membership Rewards points and 23,000 Ultimate Rewards points to Virgin Atlantic, giving him the 95,000 miles needed to book the ticket. I advised Dan to keep as many Ultimate Rewards points on hand as possible so we could transfer them to World of Hyatt or IHG Rewards to book hotels around Japan.

I ended up transferring a mixture of Citi ThankYou and American Express Membership Rewards points to Virgin Atlantic to book my award ticket. Once we both had the points in our respective Virgin Atlantic accounts, we both called back to finalize the tickets.

The same JFK-HND-ORD ticket would cost $7,751 per person if we paid for nonrefundable business-class seats. This gives us each a whopping 7.9 cents per point in value for our points after factoring out the $250 in taxes and fees — not bad for Dan's first points and miles redemption.

Oh, and if you're curious: Dan is planning to book his Chicago to New York City leg using what's left of his Spirit miles. I, on the other hand, will book a paid United ticket back to New York City in hopes of being upgraded with my lifetime United Premier Gold status.

Getting around Japan

Since we're visiting Tokyo, Kyoto and Osaka, we need a way to get between these cities and eventually return to Tokyo for our flight home. Unfortunately, ANA doesn't allow Virgin Atlantic members to book connecting tickets, so we couldn't simply book Osaka (KIX) to Tokyo to Chicago on the return.

With this in mind, we plan to spend three days in Tokyo at the beginning of the trip and take the train to Kyoto for another three-day stay. Then, we'll get back on the train for three days in Osaka and fly back to Tokyo the night before our return flight.

There is no great way to book Japanese train tickets using points and miles, so we're planning to pay cash for them closer to our date of departure. Further, an ANA flight from KIX to HND is only $74 one-way on our date of travel — we decided to pay for this flight out of pocket since using points for a cheap ticket wouldn't have made sense.

Booking hotels with Chase Ultimate Rewards points

With flights and transportation out of the way, it was time to book hotels. We needed to book hotels in all three of the cities we were visiting, as well as one night at an HND airport hotel on the way back — here's a look:

  • Tokyo - three nights
  • Kyoto - three nights
  • Osaka - three nights
  • Haneda airport hotel - one night

After booking flights, Dan and I had 97,000 and 132,000 points left in our respective Chase accounts. Chase Ultimate Rewards partners with World of Hyatt, IHG Rewards Club and Marriott Bonvoy, so we had quite a few options for booking our hotels on points. Here's a look at what we ended up booking.

Tokyo: Hyatt Regency Tokyo

(Photo courtesy of the Hyatt Regency Tokyo.)

Tokyo has a number of points hotels, but we ended up settling on the Hyatt Regency Tokyo. The hotel isn't the most centrally located, but it's close enough to Shinjuku and Shibuya and off many Tokyo metro lines that can take us around the city relatively quickly.

In addition, the hotel costs just 12,000 World of Hyatt points per night, so we only needed to transfer 36,000 Ultimate Rewards points to World of Hyatt to book a room for three nights. We transferred the points from Dan's Ultimate Rewards balance to his World of Hyatt account and booked the hotel for $0 out of pocket.

This was a pretty solid use of Ultimate Rewards points too — the three-night stay would've cost $881 if we paid cash, giving us 2.4 cents per point in value for this redemption.

Related: How to earn World of Hyatt points

Kyoto: The General Kyoto Takatsuji Fuyacho

(Photo courtesy of The General Kyoto Takatsuji Fuyacho.)

In Kyoto, we ended up booking two separate rooms at The General Kyoto Takatsuji Fuyacho. This hotel participates in the World of Hyatt program, but we ended up paying cash for our respective rooms as they were just $68 per night through Oddly enough, the hotel priced at $116 per night on the Hyatt website.

Thankfully, we're both able to earn Rewards nights on our respective stays and pay with cards that earn bonus points on hotels, so we still earn rewards for our purchase.

Related: The best hotel credit cards

Osaka: Hyatt Recency Osaka

(Photo courtesy of the Hyatt Regency Osaka.)

In Osaka, we each booked our own room at the Hyatt Regency Osaka as World of Hyatt awards are just 8,000 points per night. Since I owed Dan for the Tokyo hotel, I booked both rooms with my World of Hyatt points (transferred from Ultimate Rewards) for a total of 48,000 points for two rooms for three nights.

This is an exceptional deal when you consider that it would've cost $1,145 to book two rooms for three nights if we paid out of pocket. This means I got a nice 2.38 cents per Ultimate Rewards point in value for this redemption, 0.38 cents per point higher than TPG's Ultimate Rewards valuation.

Haneda airport: Royal Park Hotel Tokyo Haneda

(Photo courtesy of the Royal Park Hotel Tokyo Haneda.)

Unfortunately, there aren't any points hotels near Haneda airport, so I booked us a room at the Royal Park Hotel Tokyo Haneda using a Rewards certificate. A room at this hotel cost $194 during our date of travel, so I'm happy I had the rewards certificate to use.

Related: Tokyo Narita vs. Haneda: Which airport should I fly into?

Total travel costs

And that's the trip! Almost all of our travel costs and half of our hotel costs were covered using a mixture of my and Dan's points and miles, giving us a high-end trip on the cheap.

To recap, we used 95,000 transferable points and roughly $250 each to fly ANA business class round-trip from the U.S. to Japan. These tickets would've been unattainably expensive if we didn't have points, so it's pretty incredible that Dan was able to earn the points needed for this ticket by opening a couple of credit cards and meeting their minimum spending requirements.

On the hotel side of things, we collectively transferred 84,000 Ultimate Rewards to World of Hyatt to book three nights in Tokyo and Osaka. 36,000 points came from Dan's account, and 48,000 came from my account. This saved us just over $2,000, making the trip far more affordable than if we didn't have points.

Three nights in Kyoto and one night a Haneda airport hotel cost $602 total, with $194 of that being covered by a Rewards certificate. Additionally, we spent $74 per person ($148 total) on a flight from Osaka to Tokyo, and are still waiting to purchase train tickets.

This leaves us with just $1,056 spent out of pocket (plus train tickets) for travel and accommodation for a two-person, 10-day trip to Japan. This is a pretty solid redemption, especially when you consider that — if we paid for flights and all hotels with cash — we'd have spent over $18,000 for the same itinerary.

Related: Second cities: Destinations to add onto a trip to Tokyo

Bottom line

My friend Dan and I booked a 10-day trip to Japan with the help of miles and points. Before booking this trip, Dan had only been collecting points for a little over six months and — with just three rewards credit cards under his belt — was able to book his own business-class airfare to Japan and cover a chunk of our hotel stays with his points and miles.

If you're interested in doing something similar but are new to the miles and points space, don't fret — it's not too hard to get started. Start by reading TPG's beginner's guide where TPG editor Samantha Rosen shows you everything you need to know about applying for your first credit card, meeting the minimum spending and more.

Featured image by (Photo by f11photo/
Editorial disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airline or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.