CA 8443 then UA 529 at O'Hare
Anchorage → Chicago → New York LaGuardia
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
11:02UA 529 to New York LaGuardia leaves the gate
18 h 03 apart on the timetable, overnight
UA 529 leaves 18 h 03 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.