During their work, translators constantly face challenges of preserving author's intention and stylistic features of a literary work while translating original Russian texts into foreign languages. Understanding these features contributes to a more accurate perception of Russian culture with its unique images and deep meanings. This article aims to reveal the specificity of translation errors in translations of A. Chekhov's monologue ‘On the harmful effects of tobacco' into foreign languages. The original monologue and its translations into three languages (English, French and Arabic) taken from open sources were selected as the material for our study. Comparative analysis of the original and the translated versions was used to identify lexical and semantic groups of the original text that require translators' close attention: onomastic material, nominations of everyday realities related to conveying the atmosphere of the work, names of cultural realities, expressive and evaluative means. Then, based on the classification of translation errors, the main inaccuracies in translating A. Chekhov's monologue were identified: 1) violations in the transfer of meaning related to the denotative content of the text; 2) violations related to the transfer of the stylistic patterns of the original; 3) errors related to the transfer of the author's evaluation; 4) obvious violations of the norms and usage of the target language. The research also identifies the major ways of choosing an analogue: introduction of functional names, descriptive technique, the use of literal nominations, selection of an identical idiom in the target language, transcribing, calquing, etc. The study considers various aspects of semantic, syntactic and pragmatic adaptation of the material, typical for each of the three languages.