Trans-border and cross-border cooperation has become an important trend of international regionalization since the second half of the 20th century. There was a dramatic change in the geopolitical landscape of the world system in the 1990s of the 20th century: territorial systems - states, regions, cities, and districts - alongside with business firms started to join the economic competition more and more. In the last decades of the academic realm, including regional economics, there has been an increased interest in geographic limology, i.e. region cross-border cooperation. As theory and practice testify, the increase in the volume of direct foreign investments is a significant factor of the economic growth and job creation. Therefore, monitoring of the investment climate is also a significant factor which determines the state’s welfare and its development. The purpose of the article is to study the investment climate in cross- border regions in Latvia (Latgale region), Lithuania (Vilnius county, Alytus county, Utena county, Panevezys county, Kaunas county), and Belarus (Vitebsk oblast, Grodno oblast, Minsk oblast, Mogilev oblast) and to identify its differences on the basis of the survey of the representatives of small and medium-sized businesses carried out within the framework of the project “The Establishment of the United Entrepreneurship Support and Networking System for the Sustainable Latvia, Lithuania and Belarus Cross Border Cooperation”) B2B funded by the programme of Latvia-Lithuania-Belarus cross border cooperation “European Neighbourhood and Partnership Instrument 2007-2013”.