AC 8909 then CI 5233 at O'Hare
Toronto Pearson → Chicago → Anchorage
Timetable, Chicago time
17:43AC 8909 from Toronto Pearson at the gate
13:55CI 5233 to Anchorage leaves the gate
20 h 12 apart on the timetable, overnight
CI 5233 leaves 20 h 12 after AC 8909 arrives on the timetable: more than half a day, so not a connection we count.