The majority of adolescent smokers are able to purchase cigarettes even though laws prohibit the sale of cigarettes to minors (Radecki & Zdunich, 1993). The present study focused on merchant licensing, civil penalties, and monitoring of merchant behavior. Several different schedules of enforcement in the city of Chicago were evaluated to determine the optimal schedules to reduce the sale of cigarettes to minors in a major metropolitan area. Schedules of 2,4, and 6 months were effective in reducing illegal sales, from 86% to 19%, 87% to 34%, and 87% to 42%, respectively. In a control condition, illegal sales remained high (approximately 84%). Cigarette control laws that regularly enforce civil penalties for tobacco sales violations can successfully reduce minors' access to cigarettes.