IB 344 then W4 6460 at Madrid
Chicago → Madrid → Milan
Timetable, Madrid time
09:55IB 344 from Chicago at the gate
13:10W4 6460 to Milan leaves the gate
3 h 15 apart on the timetable
The last days
IB 344 and W4 6460 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.