AA 9908 then UA 2809 at O'Hare
Milwaukee → Chicago → Dallas-Fort Worth
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:40UA 2809 to Dallas-Fort Worth leaves the gate
20 h 50 apart on the timetable, overnight
UA 2809 leaves 20 h 50 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.