CA 8443 then UA 3487 at O'Hare
Anchorage → Chicago → Key West
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
11:00UA 3487 to Key West leaves the gate
18 h 01 apart on the timetable, overnight
UA 3487 leaves 18 h 01 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.