Hi! I have some questions about Canada's weather during winter because it seems to be a quite complicated season.

How cold can Winter be in Calgary, Toronto or Ottawa? Does it get unbearable or annoying? Do you usually get allergy like symptoms because of the cold?

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I've only been as far East as Calgary and only once during the winter. It hit negative 20 that time. I'm not sure what the average is, but that's the coldest I've experienced. In Southern British Columbia my coldest temperature was negative 14 and that is very rare here.
You will hear locals talk about wet cold vs dry cold. A wet cold gets through your clothes and to your bones much faster, even though the actual temperature isn't crazy like those mentioned above. In Calgary it took some time before the cold forced me inside, dry cold. Here I felt that negative 14 instantly and it didn't matter how many layers of clothing I wore, wet cold.
In terms of how tolerable it is depends on what you're used too and how fast you can acclimate. Example. My friends in Brazil start whining if the temperature gets lower than 15 Celsius. That's a nice spring day here and certainly not cold by my standards. It's not quite warm enough for a t-shirt and shorts, although it is for some people here.