AA 9908 then UA 5720 at O'Hare
Milwaukee → Chicago → Washington National
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:14UA 5720 to Washington National leaves the gate
20 h 24 apart on the timetable, overnight
UA 5720 leaves 20 h 24 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.