CA 8443 then UA 398 at O'Hare
Anchorage → Chicago → New York LaGuardia
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
15:00UA 398 to New York LaGuardia leaves the gate
22 h 01 apart on the timetable, overnight
UA 398 leaves 22 h 01 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.