[Curmudgeon]

To me, culturally and politically, Winnipeg is an eastern city in a western province. In terms of appearance, the most similar city to Winnipeg IMO is Kansas City, which also is a river city and (although the moniker is used for St. Louis) is the last industrial midwestern city before one enters the high plains and therefore the geographical Gateway to the West. Omaha also reminds of Winnipeg.

Interestingly, the two closest large cities to Winnipeg, Minneapolis and Saint Paul, both look and feel distinctly different from Winnipeg, with Saint Paul feeling like it could be in southern Ontario.