CA 8443 then UA 5565 at O'Hare
Anchorage → Chicago → Charlottesville
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:10UA 5565 to Charlottesville leaves the gate
21 h 11 apart on the timetable, overnight
UA 5565 leaves 21 h 11 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.