DL 5771 then DL 4688 at Detroit
Indianapolis → Detroit → Chicago Midway
Timetable, Detroit time
18:14DL 5771 from Indianapolis at the gate
12:30DL 4688 to Chicago Midway leaves the gate
18 h 16 apart on the timetable, overnight
DL 4688 leaves 18 h 16 after DL 5771 arrives on the timetable: more than half a day, so not a connection we count.