my mapping program shows -
since I do not know where in WI you live I mapped starting at Green Bay.
program shows 7 days at 10 hours per day driving. or 63 hours.
starting at Green Bay go North to US2, then West on US2
Into ND to Minot and then North on US52. cross border at North Portal, SK
Go North to Saskatoon, then West to Dawson Creek then Alaska Hwy.
The roads in Canada should be good with no problems, depending on road construction, etc.
Same with the Alaska hwy, traveling in late July the roads should be ok.
Go for it. With no unexpected problem should be not a problem.