Chakarov started playing for Levski's youth formations in 2002.
He made his official debut for Levski Sofia's senior team on 18 October 2008 in a match against PFC Belasitsa Petrich.
On 27 June 2009 it was announced that Chakarov would be play on loan for FC Sportist Svoge during the first half of 2009/2010 season.
On 20 January 2010, Chakarov was loaned to Chernomorets Pomorie until early December 2011.
[3] In January 2018, Chakarov returned to Spartak Pleven, taking part in the pre-season training.