AA 9908 then UA 4420 at O'Hare
Milwaukee → Chicago → Little Rock
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:29UA 4420 to Little Rock leaves the gate
22 h 39 apart on the timetable, overnight
UA 4420 leaves 22 h 39 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.