OBJECTIVES: To assess playground safety and quality in Chicago, Illinois, identify disparities in access, and use the data to inform collaborative improvement. METHODS: A cross-sectional survey of public park playgrounds in Chicago, Illinois, was conducted in 2009, 2010, and 2011 by using the National Program for Playground Safety Standardized Survey. All playgrounds were surveyed in 2009 and 2010; those that failed in 2010 were resurveyed in 2011. Playgrounds were assessed in 4 main categories: age-appropriate design, fall surfacing, equipment maintenance, and physical environment. Safety scores were generated from the assessment. Geographic information system mapping provided a visual description of the playground pass/fail rate based on neighborhood, child population, race/ethnicity, and poverty level. RESULTS: Of the ∼500 playgrounds, 467 were assessed in 2009, and 459 were assessed in 2010. In 2009, half of all playgrounds (55%) and in 2010, nearly two-thirds (61%) earned scores consistent with safe playgrounds (P < .001). Playgrounds scored poorest in fall surfacing and equipment maintenance. Geographic information system mapping showed neighborhoods with a higher percentage of children and impoverished families had fewer playgrounds and more failing playgrounds. In 2011, 154 (85%) of the playgrounds that failed in 2010 were surveyed. The mean playground score among failing playgrounds improved significantly between 2010 (61%) and 2011 (67%, P < .001). CONCLUSIONS: Since the playground improvement initiative began in 2009, considerable progress has been made in the safety scores, although access to high-quality playgrounds varies by neighborhood. Many failing playgrounds can be brought up to standard with improvement in fall surfacing and equipment maintenance.