UA 5210 then SY 8288 at O'Hare
Saginaw → Chicago → Milwaukee
Timetable, Chicago time
14:15UA 5210 from Saginaw at the gate
13:25SY 8288 to Milwaukee leaves the gate
23 h 10 apart on the timetable, overnight
SY 8288 leaves 23 h 10 after UA 5210 arrives on the timetable: more than half a day, so not a connection we count.