IB 344 then FR 2753 at Madrid
Chicago → Madrid → Milan
Timetable, Madrid time
09:55IB 344 from Chicago at the gate
08:50FR 2753 to Milan leaves the gate
22 h 55 apart on the timetable, overnight
FR 2753 leaves 22 h 55 after IB 344 arrives on the timetable: more than half a day, so not a connection we count.