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I'm doing similar, but in race simulation mode. 10 days, 1000 miles. Banff to Lima/Yellowstone area.'
Use www.eatsleepridegreatdivide.com to help plan. You can move the point A and B markers up and down the route.
Banff to Helena is 622
Banff to Butte is 686
Both should have flights to Denver and other large airports to get you back home. But, might have smaller airplanes, so getting the bike onto them, could be a problem. Missoula and Bozeman are both not far away from either town (120 miles?). Both of those cities have good flights.
I'd suggest Banff to Seeley Lake, then ride to Missoula and visit Adventure Cycling headquarters. Great city to visit and a nice way to end the trip.