AA 5008 then 5X 603 at O'Hare
Milwaukee → Chicago → Louisville
Timetable, Chicago time
09:05AA 5008 from Milwaukee at the gate
22:305X 603 to Louisville leaves the gate
13 h 25 apart on the timetable
5X 603 leaves 13 h 25 after AA 5008 arrives on the timetable: more than half a day, so not a connection we count.