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April 29, 2025 47 mins

In this episode, Jess takes us step-by-step through her family’s spring break trip to Japan—a points and miles masterpiece that cost just $200 total out of pocket for four round-trip flights and multiple hotel stays. From first class flights to washer/dryers in hotel rooms, this trip had it all. Whether you’re dreaming of cherry blossoms, bullet trains, or Hello Kitty cafés, this episode is packed with tips for making Japan happen—without breaking the bank.

Flying to Japan in Style with AA Miles

Jess booked her family’s flights using American Airlines miles, flying on Japan Airlines from Chicago to Tokyo, and shares her tips for snagging first-class saver award seats, business-class seats, and also premium-economy seats. 

Staying in Tokyo, Family Style

For the Tokyo leg, Jess chose the Hyatt House Shibuya, a new property that has quickly become her top recommendation for families. 

Kyoto on a Budget with Hyatt Place

After Tokyo, the family took the bullet train to Kyoto and stayed at the Hyatt Place Kyoto, a Category 2 gem offering amazing value. 

Activities included exploring Fushimi Inari Shrine, tasting local snacks at Nishiki Market, and spending several hours with deer at Nara Park—Molly’s favorite part of the trip!

Luxury Final Night at the Conrad Tokyo

For their final night, Jess used Hilton free-night certificates to stay at the Conrad Tokyo, a luxury property with top-tier service. From Hello Kitty water bottles at checkout to executive-lounge cocktails, it was the perfect way to end the trip. Jess doesn’t recommend it for the location alone, but if you’ve got free night certificates, she says it’s 100% worth it.

A trip to Japan for a family of four with flights and hotels for $200? This is the power of points and miles. Hit play now and hear how Jess pulled it off—and how you can too.



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