AA 2500 then CI 5233 at O'Hare
Nashville → Chicago → Anchorage
Timetable, Chicago time
17:25AA 2500 from Nashville at the gate
15:20CI 5233 to Anchorage leaves the gate
21 h 55 apart on the timetable, overnight
CI 5233 leaves 21 h 55 after AA 2500 arrives on the timetable: more than half a day, so not a connection we count.