DL 1716 then DL 5033 at Detroit
Chicago O'Hare → Detroit → Madison
Timetable, Detroit time
17:06DL 1716 from Chicago O'Hare at the gate
16:55DL 5033 to Madison leaves the gate
23 h 49 apart on the timetable, overnight
DL 5033 leaves 23 h 49 after DL 1716 arrives on the timetable: more than half a day, so not a connection we count.