AA 808 then CI 5225 at O'Hare
Washington National → Chicago → Anchorage
Timetable, Chicago time
14:29AA 808 from Washington National at the gate
08:55CI 5225 to Anchorage leaves the gate
18 h 26 apart on the timetable, overnight
CI 5225 leaves 18 h 26 after AA 808 arrives on the timetable: more than half a day, so not a connection we count.