That looks a nice journey, but does it lend itself well to a loop (is there much to see on the way back)?
No, it kinda doesn't. Not sure if Chicago will be feasible, as you say you then end up with an enormous drive back through pretty much nothing. But she really wants to visit the other side of Canada (We did West last year).
That's very useful to know - I assume it's just a case of walking in and asking to swap and they're happy to do it?
Yup, I got rid of a terrible Cadillac DTS by doing this.