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From Haneda, the Keikyu Line and Tokyo Monorail reach central Tokyo in well under an hour. From Narita, the Narita Express and Keisei Skyliner trains take roughly an hour, and airport limousine buses serve major hotels. Taxis are available but expensive, especially from Narita.
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Winter (excluding New Year) and June are often cheaper. Cherry blossom season, Golden Week and Obon tend to be the priciest times.
It varies by date and airline. Narita sometimes has lower fares, while Haneda saves time and transport cost into the city, so compare both.
The Narita Express and Keisei Skyliner are the fastest rail options, taking roughly an hour. Airport limousine buses and cheaper local trains are also available.
Yes. An open-jaw ticket into Tokyo and out of Osaka (or the reverse) is common, and the shinkansen links the two cities in a few hours.