OO 9909 then UA 4644 at O'Hare
Waterloo → Chicago → Detroit
Timetable, Chicago time
16:47OO 9909 from Waterloo at the gate
15:00UA 4644 to Detroit leaves the gate
22 h 13 apart on the timetable, overnight
UA 4644 leaves 22 h 13 after OO 9909 arrives on the timetable: more than half a day, so not a connection we count.