Urban design plays an important role in architectural education and its subdivisions. When architects are looking at cities, they not only recognize three dimensionality and geographical appearances of spaces but also see the necessity of incorporating artistic, cultural, social, environmental and psychological elements alongside. Urban design is currently studied as a fundamental discipline with the use of developing technology and influential changes in educational practices, pedagogies and methods. In this study, the artistic aesthetic principles of Hermann Maertens towards monuments and public squares are used to analyze theoretical planning of urban spaces together with technological transformations in the practice with an educational software program called Space Syntax “depth map” as a case-study to redefine the multi-disciplinary perspectives of urban design; artistic, cultural, social, psychological as well as accessibility and usability perspectives. The analysis puts forth the necessity of new multidisciplinary approaches in urban design practices and education.