DL 5680 then AA 4409 at Boston
Pittsburgh → Boston → Madison
Timetable, Boston time
20:47DL 5680 from Pittsburgh at the gate
20:28AA 4409 to Madison leaves the gate
23 h 41 apart on the timetable, overnight
AA 4409 leaves 23 h 41 after DL 5680 arrives on the timetable: more than half a day, so not a connection we count.