DL 5232 then UA 5381 at Detroit
Memphis → Detroit → Chicago O'Hare
Timetable, Detroit time
20:50DL 5232 from Memphis at the gate
14:09UA 5381 to Chicago O'Hare leaves the gate
17 h 19 apart on the timetable, overnight
UA 5381 leaves 17 h 19 after DL 5232 arrives on the timetable: more than half a day, so not a connection we count.