UA 2223 then AA 9908 at O'Hare
Tampa → Chicago → Milwaukee
Timetable, Chicago time
14:35UA 2223 from Tampa at the gate
10:00AA 9908 to Milwaukee leaves the gate
19 h 25 apart on the timetable, overnight
AA 9908 leaves 19 h 25 after UA 2223 arrives on the timetable: more than half a day, so not a connection we count.