[3] He was a leading komitaji in the bands of the Bulgarian Macedonian-Adrianople Revolutionary Committees and took part in the battles against the Ottoman authorities as well before the Ilinden Uprising as after it.

In 1901-1902 he created a channel for illegal purchase and transfer of firearms from Greece to Southern Macedonia.

As a commander of a Bulgarian guerrilla band, Chekalarov supported the Hellenic Army in the First Balkan War 1912-1913.

[4] Later he fought on the side of the Bulgarian Army on the front in Eastern Thrace in the composition of the Macedonian-Adrianopolitan Volunteer Corps.

He was killed by Greek troops during the Second Balkan War and his head was publicly displayed in Florina.