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Well, the Pacific Northwest landscapes really are quite beautiful. The one thing I dislike, however, is the dryness in the summer. The grass turns brown and makes the landscape look pseudo-Mediterranean. It's kind of a weird juxtaposition with the evergreens.
We don't get that in the Upper Midwest, where summers are verdant and humid and the grass remains green. Of course, the trade-off is winter, which is a deal-breaker for most.
Winnipeg makes more sense than Detroit or Chicago.
There are a number of decent comparisons to make here.
Vancouver vs Winnipeg (obviously Vancouver is much bigger)
MSP vs Seattle
Milwaukee vs Portland
Madison vs Eugene
Des Moines vs Spokane
Duluth vs Victoria
Smaller Northern cities: Fargo, Sioux Falls, Eau Claire, La Crosse, Rochester, St. Cloud, Cedar Rapids, Iowa City, Green Bay, Wausau, Appleton, Oshkosh, Thunder Bay, Mankato
I don't deny that Chicago fits in less with the "culture" of the the area. It's somewhat more a hodge podge of people coming from the plains and East Coast. But, having Chicago there, and all of the amenities and chabang that come with that is still certainly a perk for the region. Though, even if it was just Madison, Winnipeg, Milwaukee and Minneapolis, all of those would stand pretty well on their own.
Of course Chicago is awesome, but it isn't part of this region just like San Francisco isn't part of the PNW. Minneapolis is the anchor of the North and Seattle is the anchor of the Pacific Northwest.
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