How I Booked a $17,000 Trip to Japan for Under $100 Out of Pocket

I still remember the first time I realized credit card points were a thing. I stumbled onto a blog post from someone who flew first class to Europe for “just taxes,” and I was instantly obsessed. But once I started trying to do it myself, I hit every wall possible.

Fast forward to today – I just booked another trip to Japan (8th time!) with my partner worth $17,000, and we paid less than $100 out of pocket by having the right credit card points strategy.

Here’s exactly how we did it:

Flights: Business Class to Japan, Both Ways

✨ JAL Business Class (Outbound)

We booked Japan Airlines business class to Tokyo from LAX. US airlines could never beat that Japanese hospitality, if I’m being honest, so we fly JAL or ANA as often as we can!

✨ Singapore Airlines Business Class (Return)

Coming back, we redeemed points for Singapore Airlines business class, one of the most luxurious ways to fly long haul. The lie-flat seats, the satay skewers, the vibe? Unreal.

🏨 Hotels: 5-Star Luxury in Tokyo and Osaka

Conrad Tokyo

Our first stop is the Conrad Tokyo – a sleek, modern oasis right in the middle of the city. Massive rooms, stunning views of the bay, and breakfast that is always more like a Michelin tasting menu at Conrad properties.

Waldorf Astoria Osaka

Next up: the brand-new Waldorf Astoria Osaka. This place looks insane — ultra-refined interiors, personalized service, and the kind of calm you dream about after a day in Dotonbori. And the best part? We booked it entirely with points, making it a perfect example of Japan travel on a budget without sacrificing luxury.

💸 Total Value vs. What We Actually Paid

This entire trip – JAL and Singapore Airlines business class, 5-star luxury hotels, and unforgettable memories – would’ve cost us over $17,000 out of pocket.

Instead, we used about 580,000 points total for both of us.

That might sound like a lot – but when you’re using the best credit cards for travel rewards, maximizing the right transfer partners, booking the right dates, and stacking signup bonuses… it’s totally within reach, even if you don’t spend a ton. It only took us about 3 months to earn all of those points.

Keep Learning

Stopover Arbitrage: How to Get Two Trips for the Price of One Award Booking

Mar 28, 2026

Strategy Guide: How to Book JAL First Class to Japan with Avios

Nov 19, 2025

Strategy Guide: Booking ANA Business and First Class for As Low As 38K Points

Nov 7, 2025