He made his MLS debut for Chivas against FC Dallas on 20 April 2008, but was released by the team in February 2009.

Having been unable to secure a professional contract elsewhere, Chiles signed for Los Angeles Legends of the USL Premier Development League in June 2009.

Chiles led the Professional Arena Soccer League's Western Conference with 33 goals, helping the Sockers capture the PASL North American National Championship.

[3] Chiles earned the League MVP honor from the PASL in 2011, 2012, 2013, scoring over 200 goals in his 5-year professional indoor soccer career.

[4] Chiles has also been included in the United States Futsal National team for the last 4 years, earning 14 caps scoring 9 goals.