AA 2500 then CI 5239 at O'Hare
Nashville → Chicago → Anchorage
Timetable, Chicago time
17:25AA 2500 from Nashville at the gate
16:50CI 5239 to Anchorage leaves the gate
23 h 25 apart on the timetable, overnight
CI 5239 leaves 23 h 25 after AA 2500 arrives on the timetable: more than half a day, so not a connection we count.