DL 5771 then UA 5381 at Detroit
Indianapolis → Detroit → Chicago O'Hare
Timetable, Detroit time
18:14DL 5771 from Indianapolis at the gate
14:09UA 5381 to Chicago O'Hare leaves the gate
19 h 55 apart on the timetable, overnight
UA 5381 leaves 19 h 55 after DL 5771 arrives on the timetable: more than half a day, so not a connection we count.