AA 9908 then UA 5559 at O'Hare
Milwaukee → Chicago → Madison
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
08:45UA 5559 to Madison leaves the gate
18 h 55 apart on the timetable, overnight
UA 5559 leaves 18 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.