IB 344 then FR 3009 at Madrid
Chicago → Madrid → Milan
Timetable, Madrid time
09:55IB 344 from Chicago at the gate
06:45FR 3009 to Milan leaves the gate
20 h 50 apart on the timetable, overnight
FR 3009 leaves 20 h 50 after IB 344 arrives on the timetable: more than half a day, so not a connection we count.