CA 8443 then DL 2816 at O'Hare
Anchorage → Chicago → Boston
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
15:05DL 2816 to Boston leaves the gate
22 h 06 apart on the timetable, overnight
DL 2816 leaves 22 h 06 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.