Milan director of sport Ariedo Braida has flown to Brazil to watch Cruzeiro full-back Jonathan, according to La Gazzetta dello Sport.
The Rossoneri's need of reinforcements on the flanks has been evident for the last couple of years and finally looks likely to be addressed either in January or in June.
Braida plans to watch Jonathan, who plays at right-back, when Cruzeiro travel to play Corinthians in Sao Paulo on Saturday.
The 24-year-old does not have a European passport as of yet despite repeated attempts to obtain one and that could throw a spanner in the works.
Milan are exploring alternatives such as Benfica's Fabio Coentrao, although he is thought to be significantly more expensive than Jonathan.
Think you know your Italian football? Share your knowledge, tips and comments to win cash prizes in OLBG's tipster competition  - £11,000 to be won monthly!