New technological solutions for the effective, objective and cost-sensitive monitoring of cultural heritage are needed. Accordingly, a new methodological approach based on laser scanning, 3D photogrammetry, artificial intelligence and GIS interaction is presented in this paper. The main goal is to develop a software that could detect and compare various architectural and urban elements by comparing 2D and 3D data of objects and places of the same cultural heritage from different time periods. This represents a breakthrough technological tool for governments to track the broad-scale status of heritage and act in a timely and proactive manner. The methodological approach was to inspect changes comprised of geometrical alterations in 3D data and pixel-based information changes in 2D data. The proposed solution was developed as part of a project financed by the Research Council of Lithuania entitled Automated monitoring of urban heritage implementing 3D technologies. The first results of the project are presented in this article. All pictures and tables in this paper were prepared by the authors.