Y8 7453 then AA 4462 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
04:37Y8 7453 from Anchorage at the gate
23:00AA 4462 to Madison leaves the gate
18 h 23 apart on the timetable
AA 4462 leaves 18 h 23 after Y8 7453 arrives on the timetable: more than half a day, so not a connection we count.