He has represented Greece at youth level and has won the bronze medal in the 2015 World Military Basketball Championship.

Cheilaris started playing basketball in Leonidio BC, the team of his hometown.

[3] Following the relegation of Filathlitikos on 2014,[4] Cheilaris signed a contract with Rethymno BC of the Greek Basket League.

[7] At the end of the season he was among the team's top performers with 12.4 points, 5.0 rebounds and 1.5 steals per game.

[9] Cheilaris was also a member of the Greek squad which won the bronze medal in the 2015 World Military Basketball Championship.