CA 8443 then UA 745 at O'Hare
Anchorage → Chicago → Boston
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
15:44UA 745 to Boston leaves the gate
22 h 45 apart on the timetable, overnight
UA 745 leaves 22 h 45 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.