DL 5614 then DL 5814 at Boston
Milwaukee → Boston → New York JFK
Timetable, Boston time
18:15DL 5614 from Milwaukee at the gate
17:05DL 5814 to New York JFK leaves the gate
22 h 50 apart on the timetable, overnight
DL 5814 leaves 22 h 50 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.