AA 866 then CI 5225 at O'Hare
Boston → Chicago → Anchorage
Timetable, Chicago time
15:37AA 866 from Boston at the gate
08:55CI 5225 to Anchorage leaves the gate
17 h 18 apart on the timetable, overnight
CI 5225 leaves 17 h 18 after AA 866 arrives on the timetable: more than half a day, so not a connection we count.