AA 504 then CI 5225 at O'Hare
New York LaGuardia → Chicago → Anchorage
Timetable, Chicago time
13:19AA 504 from New York LaGuardia at the gate
08:55CI 5225 to Anchorage leaves the gate
19 h 36 apart on the timetable, overnight
CI 5225 leaves 19 h 36 after AA 504 arrives on the timetable: more than half a day, so not a connection we count.