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In terms of temperatures or sheer cold, it's Chicago. But I think Boston gets more blizzards. Chicago gets snow fairly often, but usually a small amount at a time. It doesn't get blizzards that dump like a foot at a time as often as the east coast does.
Location: northern Vermont - previously NM, WA, & MA
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at the very least Seattle is a bit greener in the winter, and you don't have to scrape or shovel rain. The excessive cloudiness does take a toll on you though, but Spring also comes much earlier in Seattle than Boston or Chicago.
I definately prefer a Seattle winter over the other two. I remember my first 2 days in Seattle when I moved there from DC. Partly cloudy and 52°. This was in early January. I thought I had died and gone to heaven! The landscape was so pretty and green. And after leaving the blustery cold colorless landscape of Maryland earlier that day I was thrilled.
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