AA 9908 then UA 5412 at O'Hare
Milwaukee → Chicago → Des Moines
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:50UA 5412 to Des Moines leaves the gate
21 h apart on the timetable, overnight
UA 5412 leaves 21 h after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.