The aim of the article is to analyze the conceptual and methodological approaches to determining the investment attractiveness of enterprises engaged in transportations. It is indicated that the investment attractiveness of transport enterprises should be determined by calculating of the overall financial situation of enterprises, which will allow potential investors to evaluate profitability and cost efficiency of its activity. An analysis of the strengths and weaknesses of the enterprise engaged in transportation can be accomplished by the evaluation of its innovative capacity. The identification of factors and reserves of the increasing of enterprise innovative development will allow distinguishing of the basic directions for the improvement of organizational and economic mechanism of its activity. With the aim of building the strategy for the strengthening of market position it is also considered important for the potential investor to obtain the information about enterprise place on the national and international markets. Political and legal environment, characterized by political stability of society and the regulatory framework of entrepreneurial and investment activity serve as a certain guarantee of the investment reliability.