Adolescent sleep research has focused heavily on duration and quality with less work examining chronotype, defined as individual differences in sleep–wake timings driven by the circadian rhythm. This study filled a gap in the literature by utilizing actigraphy-based sleep estimates in an accelerated longitudinal design in order to better understand the developmental trajectory and individual stability of chronotype during adolescence, as well as the associations between chronotype with risky behaviors, substance use, and depressive symptoms. A total of 329 adolescents (57% female; 21% Asian American, 31% European American, 41% Latino, 7% other ethnicity) provided actigraphy-based estimates of sleep and completed questionnaires at up to three time points, two years apart, beginning at 14–17 years of age. Multilevel modeling revealed a non-linear developmental trend in chronotype whereby eveningness increased from 14 to 19 years of age followed by a trend toward morningness. Individual differences in chronotype exhibited modest stability during adolescent development. Furthermore, greater evening chronotype was associated with more risky behaviors and substance use among males, and more substance use among older adolescents, whereas depressive symptoms were not associated with chronotype. The findings from this study may have practical implications for adolescent behavioral health interventions targeted at reducing risky behaviors and substance use among youth.