AA 9908 then UA 4436 at O'Hare
Milwaukee → Chicago → Springfield Branson National
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:45UA 4436 to Springfield Branson National leaves the gate
22 h 55 apart on the timetable, overnight
UA 4436 leaves 22 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.