Chekhivskyi was born on 19 July 1876, to the family of a
clergyman in the village of , in the
Kievsky Uyezd of
Kiev Governorate, Russian Empire (today in
Obukhiv Raion). In 1900 he graduated from the
Kyiv Theological Academy and the
Odesa University, from 1905 he was a
Doctor of Theology. From 1897 he was a member of the student club of
Mykhailo Drahomanov's Socialist-Democrats. From 1901 to 1905 Cherkhivsky worked as Deputy Inspector of the seminaries of Kyiv and
Kamianets-Podilskyi. Because of his activity and interest in Ukrainian nationalism at the seminaries, Chekhivskyi was dismissed and transferred to the
Cherkasy Oblast. From 1905 to 1906 he was a teacher of
Russian language as well as of the History of Literature and the Theory of Philology at the Cherkassy Theology College. Between 1902 and 1904 Chekhivskyi was a member of the
Revolutionary Ukrainian Party, after which he switched to the
Ukrainian Social Democratic Labour Party (USDLP) until 1919. In 1906, he was elected to the
Imperial Duma, however the Russian government exiled him, as a Ukrainian to
Vologda in Russia. However, through the efforts of his electors to the Imperial Duma, he was returned from exile after one year. From 1908 to 1917 Chekhivskyi lived in
Odesa where he taught in a
gymnasium as well as commercial and technical colleges. During that time he was under open police surveillance. Nonetheless, Chekhivskyi participated in the activities of a local Ukrainian
Hromada and
Prosvita association. Since 1915 he was a member of a
masonic lodge "Star of the East" that existed in
Odesa and was part of the Great East of Peoples of Russia. == Revolutionary years ==