CA 8443 then UA 5282 at O'Hare
Anchorage → Chicago → Lexington
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:50UA 5282 to Lexington leaves the gate
21 h 51 apart on the timetable, overnight
UA 5282 leaves 21 h 51 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.