Y8 7453 then AA 4416 at O'Hare
Anchorage → Chicago → Grand Rapids
Timetable, Chicago time
22:41Y8 7453 from Anchorage at the gate
22:40AA 4416 to Grand Rapids leaves the gate
23 h 59 apart on the timetable, overnight
AA 4416 leaves 23 h 59 after Y8 7453 arrives on the timetable: more than half a day, so not a connection we count.