Background: School smoking bans give officials the authority to provide a smoke-free environment, but enacting policies within the school walls is just one step in comprehensive tobacco prevention among students. It is necessary to investigate factors beyond the school campus and into the neighborhoods that surround schools. The purpose of this study was to explore the relationship between the density of tobacco retailers and the illegal tobacco sales rate within school neighborhoods and smoking behaviors among students. Methods: This study utilized secondary data from the baseline of the Youth Tobacco Access Project. Data were collected from 10,662 students attending 21 middle schools and 19 high schools, in addition to 512 tobacco retailers, all within 24 towns in Illinois during 2002. A random-effects regression analysis was performed to assess the relationship between the density of tobacco retailers and illegal tobacco sales rates on current smoking and lifetime smoking prevalence. Results: Schools had a range between 0 and 9 tobacco retailers within their neighborhood with a mean of 2.76 retailers (SD?=?2.45). The illegal sales rate varied from 0% to 100%, with a mean of 13%. The density of tobacco retailers was significantly related to the prevalence of ever smoking among students (b?=?0.09, t(29)?=?2.03, p?=?0.051, OR?=?1.10), but not to current smoking (p?greater than?0.05); the illegal tobacco sales rate was not related to current smoking or lifetime smoking prevalence (p?greater than 0.05). Conclusion: Results indicate that tobacco retailer density may impact smoking experimentation/initiation. (Contains 3 tables.)