AA 9908 then UA 5725 at O'Hare
Milwaukee → Chicago → South Bend
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:52UA 5725 to South Bend leaves the gate
23 h 02 apart on the timetable, overnight
UA 5725 leaves 23 h 02 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.