He played youth soccer with Spartacus soccer club.[1] In 2010, he began his career with the York Region Shooters in the Canadian Soccer League, and in 2011 was signed by Krylia Sovetov Samara,[2] who became interested in him through a connection with his youth coach at Spartacus, Yuri Studin.[1]
Di Chiara returned to North America in 2014 to play in the newly formed League1 Ontario with Vaughan Azzurri. He was named L1O Cup MVP during the season, after Vaughan captured the cup, defeating Sigma FC in the final.[5]
Di Chiara returned once again to Vaughan Azzurri for the 2016 and 2017 League1 Ontario seasons. With the Azzurri, Di Chiara won the 2016 League Cup and 2016 League, as well as Finals MVP, in the championship match against FC London where he helped contribute to all four of his team's goals.[9]
In June 2018, Di Chiara signed with A Lyga club FK Jonava.[11] He made his debut on June 20 in a 2–0 loss to Sūduva.[12] With the club set to be relegated, he reached an agreement with the club to release him early from his contract, allowing him to join the Canadian Premier League.[13]
York9
In January 2019, Di Chiara signed with Canadian Premier League club York9 FC.[14][15] He made his debut for York9 in their inaugural match against Forge FC on April 27, 2019.[16] Di Chiara scored his first goal for York9 on October 12 against Forge, netting a penalty to open the scoring in an eventual 4–0 victory.[17] In October 2020 York9 announced Di Chiara was leaving the club per his own request.[18]
Cavalry FC
On November 20, 2020, Di Chiara signed a multi-year contract with Cavalry FC.[19] In January 2022, it was announced Di Chiara would return for the 2022 season, his second with the club.[20] Cavalry would announce that Di Chiara would leave the club upon completion of the 2022 season.[21]