The article examines written works of John Amos Comenius and Hryhoriy Skovoroda, the outstanding educators and humanists of the 17th - 18th centuries in the context of their interpretation of the concept "freedom". The analysis of the published works of the philosophers reveals multidimensionality of this category. Specifically, freedom is viewed as a universal culture; an individual and social value; an extent of responsibility, et cetera. The research shows that these scholars established dialectical links between freedom, education, culture and humanistic thinking. Culture and erudition of a person develop under the conditions of freedom of the individual and society. Education of a person is a life-long process, it is a basis of virtuous human behaviour, morality and spirituality. John Amos Comenius Comenius and Hryhoriy Skovoroda considered school and university to perform not only educational role, but above all cultural and developmental ones. In the context of pedagogical grounds and principles of the philosophers, training and education should be appropriate to human nature and culture. A school should serve as a "workshop of humanity", which requires the activities to be well organised, the attitude to be humane, fair and impartial. Under these conditions, a school becomes a place of true paradise and pleasure as opposed to humiliation, indifference and torture. The paper underlines that the freedom of society largely determines the level of individual freedom. Freedom is an extent of teacher's responsibility.