Career
Club Russia
Di Chiara made his Russian Premier League debut for Krylia Sovetov Samara on 18 June 2011 in a game against Football Club Terek Grozny. Canada
Di Chiara returned to North America in 2014 to play in the newly-formed League1 Ontario with the Vaughan Azzuri. He was named L1O Cup Most Valuable Player during the season, after Vaughan captured the cup, defeating Sigma Football Club in the final.
Kazakhstan
In February 2015 he signed with Kazakhstan Premier League side Okzhetpes.
He made his debut against Astana on March 7. Di Chiara left Okzhetpes on 1 July 2015.
Di Chiara was called up to the Canadian senior team on September 26, 2011, for Canada"s games in the second round of CONCACAF 2014 World Cup Qualification.