AA 9950 then UA 1862 at O'Hare
Charlotte → Chicago → Punta Cana
Timetable, Chicago time
08:30AA 9950 from Charlotte at the gate
07:38UA 1862 to Punta Cana leaves the gate
23 h 08 apart on the timetable, overnight
UA 1862 leaves 23 h 08 after AA 9950 arrives on the timetable: more than half a day, so not a connection we count.