Yep!! I did this in May. Me and my bro drove from Philadelphia to Calgary. He actually came up from Florida but I only joined him in Philly. We went:
Philly- Toronto- Chicago- Sioux Falls- Billings- Calgary.
Pretty long legs... the Sioux Falls-Billings one was a good 11 hrs probably... but we stopped and checked out Mt Rushmore.
Chicago is pretty sweet... tons to see. Also, in South Dakota, you'll see about 1,000 ads for the Corn Palace along the highway. It's about as interesting as it sounds. But also kind of hilarious all at the same time..
But if you see the ads for the big ass mall... go to it... it's pretty hilarious. Forget the name of it though.
All in all though it was a pretty good trek! Good luck! You can also drive faster in the States. Your border crossing is like Sunburst or something like that at the Alberta/Montana border.
Also... turns out it's a big continent. Those maps aren't screwing around.
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