In this article, a theoretical study was carried out related to the analysis of the health insurance system in Ukraine regarding the level of its information transparency and transparency in interaction with private, cooperative clients and the state, which represents the controlling and regulatory authorities. The main goal of this study is an analytical assessment of insurance companies that provide services for voluntary health insurance in terms of openness to users of information about their economic activities, features of the offered insurance policies, their cost, etc. This paper summarizes the arguments and counterarguments within the scientific debate regarding the concept of «transparency» and the benefit received by subjects of economic relations from following the principles of openness and integrity. The urgency of solving this scientific problem lies in the fact that the level of medical protection and the quality of services provided to the population on the basis of the existing state health insurance is at a low level and does not contribute to improving the health, working capacity and quality of life of society. The study of the transparency of the health insurance system was carried out in the following logical sequence: the relevance and problematic of the researched question are determined, as well as the position of scientists regarding this is summarized; a general analysis of the dynamics of net insurance premiums and net insurance payments for 2019-2021 was carried out, for various types of insurance, including medical insurance; the activity of the most rated insurance companies in health insurance was analyzed by the level of insurance premiums and payments as of the end of 2021; a comparative analysis of the insurance products of the companies was carried out and, based on transparency indicators and a scoring system, a conditional division of the analyzed commercial institutions according to the level of information transparency into high, medium and low levels was performed, based on the obtained points with the selection of the most attractive and informationally open institutions; the final stage of the article provides conclusions and own recommendations for solving problematic aspects of the research. Informational data from the official websites of the analyzed insurance companies, open data of the National Bank of Ukraine, and statistical information on the functioning of the insurance market from the Internet became the factual basis for this study. The results of the conducted research can be helpful for individuals who are interested in choosing an insurance company for personal health insurance.