DL 5614 then DL 5689 at Boston
Milwaukee → Boston → Washington National
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
16:00DL 5689 to Washington National leaves the gate
22 h 07 apart on the timetable, overnight
DL 5689 leaves 22 h 07 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.