Walking is the most sustainable and inclusive mode of transport, offering environmental and health benefits while requiring no financial or fuel resources. Even though being an efficient mode of transport, poor pedestrian facilities and safety concerns discourage walking, especially for women, who constitute a significant proportion of pedestrians. This study, conducted in Chennai, aims to assess the urban pedestrian facilities and to understand how pedestrian-friendly a region can be from the perspective of women users. Three different routes were taken for the study. Data collection involved field observations and a questionnaire survey of women pedestrians. Based on the score of physical elements and social elements, the comfort scale of footpath was calculated by giving 50% weightage to each of the observed elements. The score thus obtained denoted that the road stretches are not pedestrian-friendly. The Structural Equation Modelling reveals meaningful relationships between observed variable and latent variable. Challenges such as obstructed footpath, lack of Kerb ramps, uneven footpath surface and poor surface quality were identified. The study emphasizes the need for gender-inclusive footpath design and pedestrian-first policies to enhance walkability, safety and inclusivity.