UA 3762 then AC 8908 at O'Hare
Manhattan → Chicago → Toronto Pearson
Timetable, Chicago time
22:41UA 3762 from Manhattan at the gate
20:40AC 8908 to Toronto Pearson leaves the gate
21 h 59 apart on the timetable, overnight
AC 8908 leaves 21 h 59 after UA 3762 arrives on the timetable: more than half a day, so not a connection we count.