AA 9908 then UA 2290 at O'Hare
Milwaukee → Chicago → Dallas-Fort Worth
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
13:30UA 2290 to Dallas-Fort Worth leaves the gate
23 h 40 apart on the timetable, overnight
UA 2290 leaves 23 h 40 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.