AA 9908 then UA 5406 at O'Hare
Milwaukee → Chicago → Grand Rapids
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:43UA 5406 to Grand Rapids leaves the gate
22 h 53 apart on the timetable, overnight
UA 5406 leaves 22 h 53 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.