i did the exact same road trip last year, except we drove from ottawa to whistler, and we went with a random person who offered her car. she was a bipolar psycho, crazy trip!
we drover ottawa-toronto-detroit-chicago-somewhere in wisconsin first night
craashed, woke up, drove to mineeapolis , chilled there for the day, then saw an atmosphere concert that night! in his hometown, at about 1130 pm, we drove over night to calgary, thorug north dakota ,saskatchewan and onto calgary. check out the plains at night... so amny stars and no pollution, amazing.
we partied in calgary for two days
then onto whis/van for the rest of the trip
try not to sleep in hotels, we only slept in 2 hotels there and back total.
make it as cheap as possible, don't eat often, only drink water and a bit of juice. granola bar and bread are your best friend. eat them when you are hungry. don't eat out, maybe 1 a day or 1 every 2 days on the roat trip have somethin cheap
that is my advice, make sure youe always above 1/4 full on gas, my gas light came on in the middle of the prairies without me realizing it, almost had to hitch hike.
thats it. bring good music, roatte drivers and dont have a schedue you have to follow.
i hope it goes well im doing the same trip this year again, cept im hiting los angeles first