AA 9908 then UA 3774 at O'Hare
Milwaukee → Chicago → Kansas City
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:15UA 3774 to Kansas City leaves the gate
22 h 25 apart on the timetable, overnight
UA 3774 leaves 22 h 25 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.