AA 9908 then UA 1357 at O'Hare
Milwaukee → Chicago → Washington
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
08:50UA 1357 to Washington leaves the gate
19 h apart on the timetable, overnight
UA 1357 leaves 19 h after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.