AA 386 then CI 5233 at O'Hare
New York LaGuardia → Chicago → Anchorage
Timetable, Chicago time
10:00AA 386 from New York LaGuardia at the gate
09:25CI 5233 to Anchorage leaves the gate
23 h 25 apart on the timetable, overnight
CI 5233 leaves 23 h 25 after AA 386 arrives on the timetable: more than half a day, so not a connection we count.