Digital technologies, which have received rapid development in recent years, are increasingly integrated into modern economic and social processes. The course towards digitalization taken by most countries is determined by the onset of a new digital era, when knowledge and information are the most important resources of the economy and are the basis for innovation. However, accelerated digitalization, as well as slowed down, carries a significant number of economic, social, political, cultural, and other threats that can be partially mitigated by creating favorable basic conditions for digital transformation. In this regard, the purpose of this study is to assess some quantitative indicators reflecting the readiness of the region's economy for digitalization. For this purpose, the integral index is calculated as the arithmetic mean of 8 sub-indices characterizing the technological provision of enterprises in the region and the affordability of information and communication technologies for them, human resources of the digital economy, the presence of a digital portrait of companies and the level of their internal digitalization, the development of e-commerce and digital networks, information security. The research is carried out in the Kaliningrad region of the Russian Federation in 2010—2018. The results of the study have shown that the level of digitalization of the economy of the Kaliningrad region correlates with the national average. The authors conclude that additional state support is required for the development of the digital economy of the region while implementing an alternative scenario of innovative development.