Construction delays increase costs of projects for contractors and owners. Planning for a construction project should include the possibility of weather-driven delays with proper likelihood approximation. This study used historical wind data in New York City and wind-related regulations for the construction industry in order to quantify the effect of wind on the on-time delivery of construction projects and the impact of regulations that limit activities in the presence of specified winds. Some regulations, implemented following a major incident lack a comprehensive understanding of their impact on the construction industry. Therefore, due to several wind-related regulations and construction wind-level limits for halting the construction or use of cranes, etc., there is a need to evaluate the consequences of these regulations on construction project schedules and timelines. In this study, two schedules for typical New York City residential buildings, 20-floor and 10-floor buildings, were created as the prototypical buildings. The impact of regulations that limit activities in the presence of specified winds is investigated with Monte Carlo analysis of wind impact on construction schedule. The analysis provided the probabilistic project duration curve, from which it is possible to determine the percentile to which the actual schedule duration corresponded. The findings emphasize the significance of considering the impact of delays caused by windy days when planning schedules, necessitating a dependable estimation grounded in real-time and localized site-specific wind data. Additionally, it highlights the potential detrimental impacts of wind level construction regulations on the extension of project timelines.