AA 5255 then OO 9912 at O'Hare
Dayton → Chicago → Richmond
Timetable, Chicago time
08:43AA 5255 from Dayton at the gate
07:30OO 9912 to Richmond leaves the gate
22 h 47 apart on the timetable, overnight
OO 9912 leaves 22 h 47 after AA 5255 arrives on the timetable: more than half a day, so not a connection we count.