CA 8443 then UA 2008 at O'Hare
Anchorage → Chicago → Orlando
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
11:23UA 2008 to Orlando leaves the gate
18 h 24 apart on the timetable, overnight
UA 2008 leaves 18 h 24 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.