CA 8443 then UA 587 at O'Hare
Anchorage → Chicago → Washington
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:21UA 587 to Washington leaves the gate
21 h 22 apart on the timetable, overnight
UA 587 leaves 21 h 22 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.