This study investigated pedestrian wind and comfort conditions in real urban configurations. The study focused on how urban special structures such as main roads, open spaces, road intersections, and street canyons affect the airflow in 11 high-density urban blocks in Bangkok’s commercial district. The wind performance was performed using a parametric platform in the Rhino-Grasshopper with Computational Fluid Dynamics (CFD) simulation plugins. It was found that open spaces significantly improved pedestrian wind comfort, while road intersections faced challenges due to restrictive configurations. Additionally, the relationship between sky view factors (SVF) and wind speeds varied across urban forms, which required specific design approaches. This study provided insights into how urban spatial configurations affected pedestrian comfort and wind ventilation. It could help urban designers and policymakers in the early stages of design-making to promote urban ventilation in high-density cities.