AA 5255 then UA 1862 at O'Hare
Dayton → Chicago → Punta Cana
Timetable, Chicago time
08:43AA 5255 from Dayton at the gate
07:38UA 1862 to Punta Cana leaves the gate
22 h 55 apart on the timetable, overnight
UA 1862 leaves 22 h 55 after AA 5255 arrives on the timetable: more than half a day, so not a connection we count.