The rising incidence of HIV infection among young men who have sex with men (YMSM) is a substantial public health concern. Traditional research on HIV among YMSM has focused largely on individual-level predictors and infrequently accounts for contextual or neighborhood-level factors such as ethnic composition and socioeconomic status. This study used neighborhood-level data from the US Census and other public sources, and individual-level data from a longitudinal cohort of YMSM in Chicago (Crew 450). Of the original 450 YMSM in the cohort, 376 reported living in Chicago (83.6 %) and were included in the analytic sample. A clustering approach was used to group the 77 community areas together by common characteristics, resulting in the identification of 11 distinct clusters. An unconditional model of individual HIV status indicated a significant amount of variance existed between neighborhood clusters (chi (2) = 21.66; p = 0.006). When individual-level variables were added to the model, only having an HIV-positive sex partner (OR = 6.41; CI 2.40, 17.1) and engaging in exchange sex in the past 6 months (OR = 3.25; 95 % CI 1.33, 7.93) were significant predictors of HIV status. Clusters with higher Walk Scores were less likely to contain HIV-positive individuals (OR = 0.94; 95 % CI 0.90, 0.98). Conversely, clusters with a larger proportion of vacant buildings were more likely to contain HIV-positive individuals (OR = 1.19; 95 % CI 1.07, 1.33). Future research among YMSM needs to investigate the mechanisms by which neighborhood of residence might influence engagement in risk behaviors or acquisition of HIV.