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I've driven it in the other direction, from Toronto to Calgary. Not much too see between Calgary/GreatFalls/Denver and the Great Lakes. Eastern Montana, N and S Dakota, Nebraska, Iowa, Saskatchewan....it all looks the same for the first 1,000 km. Boring.
If you follow the border, the biggest city between Calgary and Detroit will be Fargo (look out for wood chippers). I'd recommend driving through Canada, at least there are cities of 20,000 people or more every 4-6 hours. Or go just across the US border, turn left and head directly for Lake Superior, then following the great lakes down to Toronto. The north shore of Lake Superior is gorgeous, hilly, 2 lane roads, as is most of the drive from Thunder Bay almost all the way to Toronto.
If the wife is coming, pick a few pits stops along the way - Great Falls, Mall of the Americas in Minneapolis, Lambeau Field, etc and tell the sat system to avoid freeways.
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