UA 2031 then AA 9908 at O'Hare
Tampa → Chicago → Milwaukee
Timetable, Chicago time
15:57UA 2031 from Tampa at the gate
10:00AA 9908 to Milwaukee leaves the gate
18 h 03 apart on the timetable, overnight
AA 9908 leaves 18 h 03 after UA 2031 arrives on the timetable: more than half a day, so not a connection we count.