AA 3610 then CI 5239 at O'Hare
Toronto Pearson → Chicago → Anchorage
Timetable, Chicago time
19:41AA 3610 from Toronto Pearson at the gate
16:50CI 5239 to Anchorage leaves the gate
21 h 09 apart on the timetable, overnight
CI 5239 leaves 21 h 09 after AA 3610 arrives on the timetable: more than half a day, so not a connection we count.