I just did the drive from Calgary to Halifax, and passed through Toronto.
We went through Saskatchewan and into the States just south of Estevan until we met up with the highway...pretty much went directly east after that.
Through Minneapolis, Madison, Chicago, skirted around Detroit, and up into Ontario.
Took about 4 days from Calgary to Montreal, so you're probably looking at 3 long days, or 4 reasonable days of driving.
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