CV 21 then UA 662 at O'Hare
Anchorage → Chicago → Toronto Pearson
Timetable, Chicago time
22:27CV 21 from Anchorage at the gate
21:21UA 662 to Toronto Pearson leaves the gate
22 h 54 apart on the timetable, overnight
UA 662 leaves 22 h 54 after CV 21 arrives on the timetable: more than half a day, so not a connection we count.