Having cycled extensively in both cities let me just say - the two cities (calgary and TO are different).

The suburban parts of each city are hell on wheels - they both suck period.

The MUP's in calgary are both more extensive and nicer to ride on than the ones in toronto.

Toronto city streets are much nicer to ride on than Calgary city streets

My average speed in Calgary is higher than in Toronto - because I'm mostly on MUP's that require no stops.

Calgary has much fewer 4-way stops in residential areas, which is waaay better than the 4-way stops in toronto (unless you blow them, but that's an Advocacy topic

Toronto is more flat.

Calgary has more ice.

Either city is pretty good for cycling, but people are more receptive to utilitarian cycling in Toronto. And there are a lot of LBS's who will do repairs and tune ups while U wait in toronto (In calgary I've been told to wait a week - that's not OK if you are using your bike to get around - and no they don't have a loaner for the week that you're waiting)