Walking is correlated with both improved physical and emotional health. However, walking behavior is often heavily influenced by environmental conditions. The goal of this study was to examine actual and perceived walkability safety and the relationship between perceived walkability safety and self-rated levels of walkability participation, defined as the number of places one walks within the community on a regular basis. Researchers used a mixed-methods approach, combining direct observations of traffic safety and in-person surveys within a specific Chicago neighborhood from 2015 to 2016 and from 2016 to 2017, respectively. We conducted behavioral assessments on 25 intersections and 48 sidewalks and surveyed 96 pedestrians on perceived walkability safety and walkability participation. Findings showed 68% and 81% of vehicles in 2015 and 2016, respectively did not obey street signs, placing pedestrians at significant risk. Pedestrians expressed concerns about the safety of walking in their neighborhood yet walked to a median of eight places weekly. The results indicated a marginally significant positive relationship between self-reported community participation and walking habits, as well as relationships between various factors of perceived walkability and age, gender, or language of survey completion. It is clear from the results of this study that walkability in this community is not a safe activity. However, walking habits may also be influenced by community satisfaction and SES factors. Communities need to engage in safe driving campaigns and educate walkers on how to protect themselves from distracted drivers. Local governments should implement policy initiatives such as police enforcement and drivers' education campaigns.