AA 4460 then K4 221 at O'Hare
Madison → Chicago → Cincinnati Northern Kentucky
Timetable, Chicago time
11:10AA 4460 from Madison at the gate
10:35K4 221 to Cincinnati Northern Kentucky leaves the gate
23 h 25 apart on the timetable, overnight
K4 221 leaves 23 h 25 after AA 4460 arrives on the timetable: more than half a day, so not a connection we count.