CA 1055 then UA 662 at O'Hare
Anchorage → Chicago → Toronto Pearson
Timetable, Chicago time
22:20CA 1055 from Anchorage at the gate
21:21UA 662 to Toronto Pearson leaves the gate
23 h 01 apart on the timetable, overnight
UA 662 leaves 23 h 01 after CA 1055 arrives on the timetable: more than half a day, so not a connection we count.