[Bishop2047]

Fun question and your answer will depend on your perspective of Canada.

If you could put Edmonton, Halifax, and Montreal into a blender the product would be a pretty darn Canadian city IMO, though I don't know if I would use any of the three to exemplify Canada alone, except Halifax.

Most: Kamloops (Mountains, skiing, nature)
Saskatoon (Farming, Rivers, small town folks living in a city)
Saint John NB or Halifax (Port city, British influences in architecture)

Least: Quebec City (Intentionally tries not to be a typical Canadian City)
Windsor (Feels more connected to the US than the rest of Canada)
Victoria (Weather/location/general vibe of the city are not stereotypical
Canadian)