Balmy Edmonton ranks first with a high score, followed by Vancouver,Toronto, Winnipeg and Ottawa (dead last).
Some observable generalizations for winter:
Edmonton can alternate between severe cold and weather-wise winter warmth -- the cold snaps are typically fairly brief; the warm spells endure.
Vancouver while mild for most of the winter is persistently "wet", overcast and has high humidity. It is ideal from a low wind perspective
Winnipeg can also experience periods of extreme cold that can last longer than Edmonton's negatives.
Ottawa gets a ton of snow and with occasional high winds can see the white stuff drift to form snow berms.
Toronto while typically milder than all but Vancouver has consistently high icy winds off of Lake Ontario.
All said, the Canadian differences between cities is less pronounced than what gets chatted about from a weather perspective, anecdotally -- a solid reason why Edmonton should embrace its "winterness" and turn it into a mega-sized positive.