AA 9908 then UA 1540 at O'Hare
Milwaukee → Chicago → San Jose (California)
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
09:02UA 1540 to San Jose (California) leaves the gate
19 h 12 apart on the timetable, overnight
UA 1540 leaves 19 h 12 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.