AA 581 then CI 5225 at O'Hare
Miami → Chicago → Anchorage
Timetable, Chicago time
09:30AA 581 from Miami at the gate
08:55CI 5225 to Anchorage leaves the gate
23 h 25 apart on the timetable, overnight
CI 5225 leaves 23 h 25 after AA 581 arrives on the timetable: more than half a day, so not a connection we count.