AA 9908 then UA 1448 at O'Hare
Milwaukee → Chicago → Houston
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:40UA 1448 to Houston leaves the gate
22 h 50 apart on the timetable, overnight
UA 1448 leaves 22 h 50 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.