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Hi.
May i know will it be too cold to travel to Osaka and Tokyo with kids 6 and 9 years old from 15dec to 30dec? Will many attraction/places closed due to winter at this period of time? Too cold to walk in streets? As for Disneyland, will all the station be open? Too cold for queuing and waiting for rides?
Is it better to go from late Nov to mid Dec? Or actually no differences?
Just wear enough layers, and you and your kids will be fine.
Tokyo and Osaka don't have any attractions that close during winter AFAIK, but most places (including shops and malls) certainly close earlier for the days during winter season. That's something to bear in mind when planning the itinerary.