AA 4669 then UA 1066 at O'Hare
Madison → Chicago → Houston
Timetable, Chicago time
08:00AA 4669 from Madison at the gate
17:30UA 1066 to Houston leaves the gate
9 h 30 apart on the timetable
The last days
AA 4669 and UA 1066 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.