How I Booked a 3-Week Honeymoon to Japan With Points and Miles

After several months of planning, my wife and I got married in Toronto, Canada. While the wedding was fun, I was more excited about planning our a honeymoon.

I wanted to make this trip special, flying to our destination and back in a premium cabin and staying at some luxury hotels along the way. Fortunately, I have earned millions of points and miles over the years to make this possible. On top of that, I had some hotel free night certificates available.

Although I have visited Japan several times, the country has always stood out. Of the more than 100 countries I have traveled to, Japan is my favorite by a mile. It has fantastic cuisine, a deep history, natural beauty, and incredibly welcoming people.

Naturally, I wanted to share my love of my favorite country with my wife, to whom I have told hundreds of stories about Japan.

Since she had never been to Japan before, I thought our honeymoon would be the perfect time for her first visit. Here’s a look at the flights and hotels I booked using points and miles for my honeymoon trip to Japan.

Booking Honeymoon Flights to Japan

Finding award flights in business or first class internationally requires a great deal of flexibility. This often means either booking your flights an entire year ahead of time or, conversely, snagging them at the very last minute.

For our honeymoon, we opted for the latter approach. While a riskier choice, but as you’ll read below, it panned out quite well for us.

Since we were dead set on visiting Japan for our honeymoon, the first step was to look at what airlines we wanted to fly and if there was award space. I decided to book one-way award tickets as I was sure I would find some flights to get us back to Chicago after the honeymoon.

United Polaris and SWISS Business Class to Japan

Since I live in Chicago, I began looking up award space from Chicago O’Hare International Airport [ORD] a couple of days before the wedding.

I hoped to secure premium cabin award space with ANA (All Nippon Airways) and Japan Airlines, as they are 2 of my favorite airlines. Unfortunately, I couldn’t find any last-minute availability with either airline.

That led me to Plan B. I looked at several airlines and their loyalty programs to see the best way to fly to Japan and found numerous options for flying between Chicago and Tokyo.

Ultimately, I chose to book Star Alliance awards with Air Canada’s Aeroplan loyalty program, which has among the best award rates for partner redemptions and a distance-based award chart for partner awards. I was able to find award space with a single layover in Zurich. Best of all, we would be flying business class on 2 different airlines: United and SWISS. Even though I had previously flown both airlines in premium cabins, this would be my wife’s first experience in business class.

To calculate the Aeroplan points I needed for this specific award redemption, I looked at the award chart for flights between North America (U.S. or Canada) and Pacific zones (Japan). Then, I used the Great Circle Mapper tool to calculate the total distance for the itinerary.

The one-way business class award redemption to Tokyo cost 87,500 Aeroplan points and CA$102 (about $76) in taxes and fees per person. Although that may seem like many points for a one-way business class ticket, it paled compared to the cash price, which was north of $6,500 per person.

The first flight between Chicago and Zurich (ZRH) was in United Polaris business class. Although not my favorite business-class product, United Polaris has much to offer, including excellent privacy, decent onboard cuisine, and a lie-flat bed.

After landing in Zurich, we had a couple of hours to enjoy the SWISS Business Class Lounge while we waited for our next flight. The flight from Zurich to Tokyo was on a SWISS Airlines Boeing 777-300ER.

Despite having mediocre business class experiences on other Lufthansa Group Airlines (Lufthansa and Austrian Airlines), SWISS business class was much better than I expected.

Emirates First Class to Chicago

After more than 3 weeks in Japan, it was time to return home. I began looking for award space toward the end of the trip, hoping we could fly ANA or Japan Airlines back to Chicago. Unfortunately, there was very limited last-minute award space in premium cabins with either airline once again.

I wanted to fly on a new airline or premium cabin product. After looking at numerous options, I found one of the most sought-after award redemptions in the points and miles world: Emirates first class.

Booking Emirates first class with points and miles has always been relatively difficult, but it has only gotten more difficult in recent years.

Since Emirates is not a member of one of the 3 major airline alliances, there are limited ways to book Emirates first class. Emirates has partnerships with individual airlines, such as Air Canada Aeroplan and Qantas Frequent Flyer. However, booking Emirates first class awards with partner programs is difficult as Emirates has greatly restricted partner first-class award space over the years.

Ultimately, I booked Emirates first class through Emirates’ loyalty program, Emirates Skywards. Although the program has undergone multiple devaluations over the years, the program is best when it comes to award availability.

After logging in to my Emirates Skywards account, I began looking for award space from both Tokyo airports, Narita Airport (NRT) and Haneda Airport (HND), to Chicago O’Hare International Airport (ORD). Fortunately, I was able to find award space relatively easily. Best of all, this itinerary featured first class flights on both an Emirates Airbus A380 and an Emirates Boeing 777.

I booked this itinerary for 187,500 Emirates Skywards miles and approximately ¥190,000 (about $1,350) in taxes and fees per person. Despite the high miles required and the taxes and fees, I was eager to experience Emirates first class.

Emirates has one of the best first-class products in the world. It features some of the best inflight dining and cabin crew service in the sky. It also boasts some fun perks, such as the shower suite and the onboard bar on the A380.

Hot Tip:

Although the Emirates 777 does not feature an onboard shower or bar, it does offer many unique in-seat features and amenities like a private minibar. Of course, you can expect an incredible dining experience in Emirates first class, regardless of the aircraft you’re flying on.

Booking Hotels in Japan

Along with our flights, we reserved several hotels using points and free night certificates. To conserve our points, however, we opted to use them for just a few nights.

I wanted to show my wife many different experiences, so we chose a mix of local hotels, capsule hotels, and even a few hostels for the remaining 20 nights that weren’t bookable with points. Here’s a glimpse at some of the hotels we did end up booking using our points and free night certificates.

Conrad Tokyo (Hilton)

The first hotel we booked was Conrad Tokyo, using a free night certificate from the Hilton Honors American Express Aspire Card*. The Hilton Aspire card’s free night certificate is incredibly valuable as it can be used at almost any Hilton property worldwide as long as it has Standard Room Reward award space.

*The information regarding the Hilton Honors American Express Aspire Card was independently collected by Upgraded Points and not provided nor reviewed by the issuer.

My stay at Conrad Tokyo was exceptional. The hotel provided outstanding Japanese hospitality, and I had the best breakfast I’ve ever enjoyed at a hotel. As a Hilton Honors Diamond Elite member (a perk of the Hilton Aspire card), I was also upgraded to a nicer room.

Bottom Line:

The Conrad Tokyo is now among my favorite hotels in the world. I will absolutely stay here again, and I can’t wait to redeem Hilton Honors points for my future stays.

The Ritz-Carlton, Tokyo (Marriott)

We also booked a night at The Ritz-Carlton, Tokyo, thanks to a free night award from the Marriott Bonvoy Brilliant^® American Express^® Card.

Unlike the Hilton Aspire card free night certificate that can be used at almost any Hilton property worldwide, the free night award from the Marriott Bonvoy Brilliant card has more restrictions. The free night award gives cardholders a reward night at any hotel participating in Marriott Bonvoy, up to 85,000 points.

The Ritz-Carlton, Tokyo, is one of Tokyo’s most well-known and luxurious hotels. Property cash rates often exceed $1,000 per night for a standard room. With high cash prices, using a free night award can provide excellent value.

As expected, the hotel was incredible. Since I have Marriott Bonvoy Platinum Elite status, I received some benefits, including a room upgrade, a 4 p.m. late checkout, and an in-hotel welcome gift.

Caption by Hyatt Namba Osaka (Hyatt)

After an incredible week in Tokyo, we headed to Osaka, where we stayed 2 nights at the Caption by Hyatt Namba Osaka, a new Category 1 Hyatt property that opened earlier this year.

Category 1 World of Hyatt properties can be booked starting at 3,500 points per night (off-peak) and as high as 6,500 points per night (peak). Our dates fell in the standard season, so we booked for 5,000 points per night.

Since cash rates were quite high, we opted to redeem World of Hyatt points.

Although I did not have too many expectations for the Caption by Hyatt Namba Osaka as a Category 1 Hyatt hotel, I was pleased with the property. It boasted an ideal Namba location near many of Osaka’s top tourist attractions.

The rooms were relatively spacious, albeit not nearly as luxurious as those at the previous hotels. Still, I would stay here again if I had the opportunity, as the property had great value, particularly when redeeming World of Hyatt points.

Hyatt House Tokyo Shibuya (Hyatt)

Lastly, I booked 1 night at the Hyatt House Tokyo Shibuya, courtesy of a Category 1-4 free night certificate from The World of Hyatt Credit Card. I chose the Hyatt House Tokyo Shibuya because of its fantastic location in the newly developed part of Shibuya.

After confirming standard award space was available, I booked the Category 4 hotel using my certificate. Cash rates for this property routinely exceed $400, providing excellent value from the free night certificate.

As a World of Hyatt Globalist member, I was entitled to some benefits, including complimentary breakfast and a 4 p.m. late checkout. Although the room was somewhat basic, I appreciated that it featured a laundry machine, which was quite convenient.

Final Thoughts

Our honeymoon in Japan was incredible. The country has so much to offer, and I am glad we were able to spend nearly a month in my favorite country. Best of all, we saved thousands of dollars on flights and hotels, which we instead used on experiences and meals while in Japan.

Fortunately, we could fly there and back in premium cabins on some of the better airlines in the world. While United Polaris and SWISS business class were fun experiences, Emirates first class was incredible.

We also stayed at some of the best hotels in the world, including The Ritz-Carlton, Tokyo, and Conrad Tokyo, the latter of which is now one of my favorite hotels. This honeymoon was a dream come true, and I can’t wait to do something like this again.