AA 9908 then AC 8904 at O'Hare
Milwaukee → Chicago → Toronto Pearson
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:50AC 8904 to Toronto Pearson leaves the gate
23 h apart on the timetable, overnight
AC 8904 leaves 23 h after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.