AA 4669 then SY 8288 at O'Hare
Madison → Chicago → Milwaukee
Timetable, Chicago time
08:00AA 4669 from Madison at the gate
13:25SY 8288 to Milwaukee leaves the gate
5 h 25 apart on the timetable
The last days
AA 4669 and SY 8288 weren’t both flown 15 min to 12 h apart in the last 21 days.
Statistics from past flights, not live flight information. Always check times and your connection with your airline, and don’t base travel or booking decisions on these numbers.