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To assess youth's ability to purchase alcohol in a city previously not assessed—Chicago, Illinois—we hired individuals aged 21 and older who appeared to be aged 18–20 (i.e., pseudo-underage buyers) to make alcohol purchase attempts without age identification in off-premise licensed alcohol establishments. We conducted two purchase attempts at each establishment across 44 community areas, resulting in a total of 652 purchase attempts. Our dependent variable was purchase attempt outcome (purchase, no purchase) and we used four categories of independent variables: characteristics of sellers, establishments, purchase attempts, and community areas. We analyzed our data using a logistic regression model, with purchase attempt outcome regressed on the independent variables. The overall purchase rate was 35.1%, ranging from 0% to 72% across community areas. Buyers were less likely to purchase alcohol in community areas that had populations with higher percentages of Hispanics (OR = 0.99; CI = 0.98, 1.0), and more likely to purchase alcohol in establishments that had more expensive beer (OR = 2.0; CI = 1.50, 2.67) and in areas with higher percentages of unemployed individuals (OR = 1.1; CI = 1.07, 1.14). Although progress has been made since the early 1990s in reducing sales to underage youth, youth still have relatively easy access to alcohol from licensed establishments. We recommend increased use of compliance checks—underage youth attempt to purchase alcohol under the supervision of enforcement agents; if alcohol is sold, the server/seller and/or license holder are penalized—which scientific studies have shown to be the most effective strategy in reducing sales to minors.