AA 9908 then UA 1486 at O'Hare
Milwaukee → Chicago → Washington
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:32UA 1486 to Washington leaves the gate
20 h 42 apart on the timetable, overnight
UA 1486 leaves 20 h 42 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.