UA 2433 then DM 5421 at O'Hare
Boston → Chicago → Punta Cana
Timetable, Chicago time
22:29UA 2433 from Boston at the gate
11:10DM 5421 to Punta Cana leaves the gate
12 h 41 apart on the timetable, overnight
DM 5421 leaves 12 h 41 after UA 2433 arrives on the timetable: more than half a day, so not a connection we count.