IB 344 then W4 6314 at Madrid
Chicago → Madrid → Milan
Timetable, Madrid time
09:55IB 344 from Chicago at the gate
23:10W4 6314 to Milan leaves the gate
13 h 15 apart on the timetable
W4 6314 leaves 13 h 15 after IB 344 arrives on the timetable: more than half a day, so not a connection we count.