DL 4688 then WN 1582 at Detroit
Chicago Midway → Detroit → St Louis
Timetable, Detroit time
15:44DL 4688 from Chicago Midway at the gate
14:55WN 1582 to St Louis leaves the gate
23 h 11 apart on the timetable, overnight
WN 1582 leaves 23 h 11 after DL 4688 arrives on the timetable: more than half a day, so not a connection we count.