AA 9908 then G7 166 at O'Hare
Milwaukee → Chicago → Madison
Timetable, Chicago time
08:20AA 9908 from Milwaukee at the gate
10:55G7 166 to Madison leaves the gate
2 h 35 apart on the timetable
The last days
AA 9908 and G7 166 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.