Whichever route you take, Fort McMurray to Windsor (Ontario) is over 3400km. Use satellite and streetview on https://www.googlemaps.com to follow each route to see which one is best for you. The route which crosses the border at North Portal and passes through Minneapolis and Chicago takes a minimum of 32 hours driving time (not including time spent at border crossings). The route which passes through or near Portage la Prairie, Winnipeg and Sault Ste Marie (Michigan) takes a minimum of 36 driving hours (not including time spent at border crossings).
