CA 8443 then UA 460 at O'Hare
Anchorage → Chicago → Jacksonville
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:29UA 460 to Jacksonville leaves the gate
21 h 30 apart on the timetable, overnight
UA 460 leaves 21 h 30 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.