CA 8443 then UA 5992 at O'Hare
Anchorage → Chicago → Washington National
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
15:00UA 5992 to Washington National leaves the gate
22 h 01 apart on the timetable, overnight
UA 5992 leaves 22 h 01 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.