DL 8868 then AA 9908 at O'Hare
Tampa → Chicago → Milwaukee
Timetable, Chicago time
14:54DL 8868 from Tampa at the gate
10:00AA 9908 to Milwaukee leaves the gate
19 h 06 apart on the timetable, overnight
AA 9908 leaves 19 h 06 after DL 8868 arrives on the timetable: more than half a day, so not a connection we count.