Chap with Italian article in Italian city (5)
I believe the answer is:
milan
'italian city' is the definition.
(city in Italy)
'chap with italian article' is the wordplay.
'chap' becomes 'man' (chap can mean a man).
'with' is an insertion indicator.
'italian article' becomes 'il' (the definite article in Italian).
'man' enclosing 'il' is 'MILAN'.
'in' is the link.
(Other definitions for milan that I've seen before include "City of northern Italy" , "Italian city with La Scala opera house" , "Northern Italian city" , "Capital of Lombardy" , "N. Italian city" .)