The effective management of risks in urban construction projects is a critical factor for ensuring timely completion, cost efficiency, and adherence to quality standards. As urbanization continues to expand, the complexity and scale of construction projects in urban environments create increasingly significant challenges. Existing literature addresses various aspects of risk management in construction, yet there is a notable gap concerning how contextual factors per differing geographical and cultural settings impact risk management strategies. This study focuses on understanding and analyzing these influences within the specific contexts of Uppsala, Sweden, and Chicago, USA. This research is taken on through a comparative case study approach with the integration of qualitative methods including semi-structured interviews with project managers and an in- depth project document analysis. Four interviews were conducted with project managers in Uppsala and Chicago, supplemented by additional interviews with project managers in Västerås, Sweden, and another in Chicago. The project documents for the Uppsala Light Rail project were also analyzed to provide a detailed understanding of risk management practices in this specific case. The study addresses effective risk management in urban construction projects and the adjusted approaches used that consider both internal and external contextual factors. By applying theoretical models such as De Meyer’s Model of Uncertainty, Contingency Theory, and Hofstede’s Cultural Dimensions Theory, this research bridges the gap between theory and practice by providing realistic insights and recommendations for project managers and researchers within this field. This study enhances our understanding of how contextual factors influence risk management in urban construction projects. It also speaks of the importance of adapting risk management strategies to the specific conditions of each project, with an emphasis placed on the need for flexibility, continuous communication, and the integration of practical risk management methods. The findings contribute to the field by offering insights into best practices in correlation with cultural and geographical considerations toward developing effective risk management approaches.