Travelling with Greyhound buses in Canada
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I work for Busbud, a bus booking app based in Montreal. We currently (August 2018) don't support Greyhound Canada's ISIC discount (hopefully we can soon). We do have some tools that may help you compare and find other bus companies where available, and search across various stops within each city.
It's odd that you aren't able to book two ISIC tickets on Greyhound.ca but I'm seeing the same thing. Note that Greyhound.ca has entirely different mobile and desktop websites, you could try both. I suppose you could book each ticket separately if nothing else works.
AFAIK the Greyhound App is only supported on the US side, it may work for buses crossing the border but likely doesn't work for Greyhound Canada within Canada.
Tickets usually cost more close to departure, how much varies by route. The maximum price you'll have to pay should match the "Standard Fare" displayed on greyhound.ca. More significantly, buses often sell out on weekends and other peak travel times, so consider booking ahead.
Also note that Greyhound is cancelling all routes west of Sudbury Ontario at the end of October 2018.
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