AA 386 then CI 5225 at O'Hare
New York LaGuardia → Chicago → Anchorage
Timetable, Chicago time
10:00AA 386 from New York LaGuardia at the gate
08:55CI 5225 to Anchorage leaves the gate
22 h 55 apart on the timetable, overnight
CI 5225 leaves 22 h 55 after AA 386 arrives on the timetable: more than half a day, so not a connection we count.