AA 5501 then CI 5239 at O'Hare
White Plains → Chicago → Anchorage
Timetable, Chicago time
18:30AA 5501 from White Plains at the gate
16:50CI 5239 to Anchorage leaves the gate
22 h 20 apart on the timetable, overnight
CI 5239 leaves 22 h 20 after AA 5501 arrives on the timetable: more than half a day, so not a connection we count.