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Having been to both Osaka/Japan and Chicago, I would say while I prefer NYC to Tokyo(my two favorite cities in the world anyways), I do prefer Osaka to Chicago.
This is coming from a person that adores Chicago and lives just outside of Tokyo....I think a lot of people tend to forget Osaka is the size of NYC (and just as urbanely built), so it's going to take most of the poll off of size alone.
....That being said, Chicago would without question take the architecture & downtown gold medal home between the two (Osaka like Tokyo lacks a traditional downtown/core)
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