AA 9866 then UA 5933 at O'Hare
Bloomington-Normal → Chicago → Milwaukee
Timetable, Chicago time
13:11AA 9866 from Bloomington-Normal at the gate
12:29UA 5933 to Milwaukee leaves the gate
23 h 18 apart on the timetable, overnight
UA 5933 leaves 23 h 18 after AA 9866 arrives on the timetable: more than half a day, so not a connection we count.