DL 5614 then DL 2887 at Boston
Milwaukee → Boston → Orlando
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
15:34DL 2887 to Orlando leaves the gate
21 h 41 apart on the timetable, overnight
DL 2887 leaves 21 h 41 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.