DL 5680 then UA 2433 at Boston
Pittsburgh → Boston → Chicago O'Hare
Timetable, Boston time
20:45DL 5680 from Pittsburgh at the gate
20:25UA 2433 to Chicago O'Hare leaves the gate
23 h 40 apart on the timetable, overnight
UA 2433 leaves 23 h 40 after DL 5680 arrives on the timetable: more than half a day, so not a connection we count.