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Airfare deal: Los Angeles LAX to Nagoya NGO Japan on Air Canada $442 total Round trip all-in
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Trains stop running around midnight/1am and start up around 5am? There's some limited night bus service that runs from the airport to downtown Night Bus N10 (12am-5am). No surcharge for the bus.
I did find one flight with a short 4hr layover, but it was $477.
Air Canada probably isn't the best airline for Asian long haul, but it's a lot better than any American based carriers. For flights to Asia, I'd recommend, ANA, Singapore, Cathay Pacific, but you're not going to find those airlines at this price. Would be $700+.
Nagoya is the perfect middle point between Tokyo and Osaka. Cheapest way to get to get to either city is by a night bus, but the bus ticket will cost about $30-60 one way. More expensive options are limited-express trains, local flights, and the bullet train shinkansen.
September-October is probably the second best time to visit Japan. The temperatures are cooling down, but hasn't become really cold yet. Only thing to worry about is typhoons and rain. April/May is the best time, perfect spring weather and (Hanami) sakura blooming, but travel/hotels are crazy expensive because of Golden Week Holiday.