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Personally, I see more climate similarities than differences. They're both awful in an August heat wave. They're both brutal in a midwinter cold snap if it's windy and high humidity. I don't have enough first hand experience with Chicago to have an opinion.
They're similar, but not identical. Chicago has noticeably colder winters, which is the main reason why New York is stomping this.
Yeah not enough cold winter fans on this board!
All in all I would say very similar for 8+months out of the year. You probably wouldn't notice much of a difference.
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