DL 5232 then WN 2631 at Detroit
Memphis → Detroit → Chicago Midway
Timetable, Detroit time
20:50DL 5232 from Memphis at the gate
13:30WN 2631 to Chicago Midway leaves the gate
16 h 40 apart on the timetable, overnight
WN 2631 leaves 16 h 40 after DL 5232 arrives on the timetable: more than half a day, so not a connection we count.