CA 8443 then UA 2287 at O'Hare
Anchorage → Chicago → Sarasota
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
11:44UA 2287 to Sarasota leaves the gate
18 h 45 apart on the timetable, overnight
UA 2287 leaves 18 h 45 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.