CA 8443 then UA 5915 at O'Hare
Anchorage → Chicago → Toronto Pearson
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
15:47UA 5915 to Toronto Pearson leaves the gate
22 h 48 apart on the timetable, overnight
UA 5915 leaves 22 h 48 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.