Chronotype refers to individual differences in sleep timing and in preferences for a given time of day while sleep duration refers to the hours of sleep. Here, we assessed chronotype, sleep duration, and nightmare frequency in relation to the Big Five personality factors. Overall, 2,492 persons (1,437 women, 1,055 men) completed the online survey between March 23, 2015, and April 8, 2015. The mean age of the sample was 47.75 ± 14.41 years. In bivariate correlations, age, extraversion, agreeableness, and conscientiousness were related to morningness, and openness to experience and neuroticism were related to eveningness. In the multiple regression, gender, neuroticism, and agreeableness were not related to chronotype. Morning types slept less at weekends than evening types, and evening types showed longer sleep latencies. Neuroticism showed the strongest effect on nightmare frequency followed by openness to experience. Nightmare frequency declined with age, and there was a small but significant effect of conscientiousness on nightmare frequency; persons with higher conscientiousness scores reported slightly more often nightmares. Chronotype was not associated with nightmare frequency. To conclude, chronotype is associated with personality factors and sleep behavior (sleep duration on weekends and sleep latency).