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Not as obvious as Vancouver/Seattle (yeah, I know they're different and unique and all that, but certainly the easiest match) What US city does Winnipeg resemble most in terms of urban form and feel?
Omaha easily. Winnipeg and Omaha have a similar metro population, Omaha is slightly bigger. They are both pretty flat, Winnipeg is flatter though. A lot of neighborhoods have a similar look to them, and both cities have major rivers running through them.