Čakarević started his professional career with the French team ASVEL, where he played from 2006 to 2008.

In January 2009, Čakarević joined the Macedonian side Pelister, but returned to his homeland in March 2009, when he signed for Swisslion Takovo.

[4] In the preseason tournament played in Valjevo, he injured his shoulder, injury that will likely keep him off the court the entire season.

[7] In February 2017, he signed with Serbian club Dynamic for the rest of the season.

[8] He was named the MVP of the Serbian Super League's 2017 season.