The purpose of this study was to determine how political instability influences inbound tourist flows in Ukrainian cities, performance of tourism-related businesses, and tourism-based profits in general. This study allows us to present the impact of various events on the tourism economy in Ukraine; however, the available secondary data with the unobserved component model procedure detection give only a general overview of the situation. Thus, interviews were conducted with experts, including managers of accommodation facilities, employees of municipal tourism development departments, and researchers investigating tourism. Interviews with experts revealed opportunities, threats, and future scenarios of tourism in Ukraine in the face of five years of political instability. The results support previous findings that political instability reduces tourist traffic over the short term. On the other hand, the interviews with experts representing major province cities have shown different results for the long-term perspective. Cities with developed tourism sectors in areas away from the place of conflict are beneficiaries of political instability. Disadvantaged are cities that had their tourist flows based on the citizens of the aggressor’s country—the Russian Federation. Cities that are underdeveloped in terms of tourism did not experience a significant impact of the political instability in eastern Ukraine.