© International Headache Society 2018. Objective: To evaluate the prevalence and characteristics of headache and its relationship with comorbidities and lifestyle in a teenage population. Methods: This is a cross-sectional study. Data was collected from students aged 12–18 years from six different schools in Catalonia, Spain. They completed an anonymous questionnaire with demographic, lifestyle, medical data, presence of recurrent headaches and its features, and completed the Strengths and Difficulties Questionnaire. We defined probable migraine if headache presented ≥ 3 ICHD-3 beta criteria for migraine. An analysis was performed to evaluate headache characteristics and compare lifestyles between those with or without headache. Results: 1619 out of 1873 students completed the survey (response rate 86.4%). From these, 30.5% suffered from recurrent headache and 11.3% had migraine features; 32.9% of adolescents with headache had at least one episode per week and 44.1% showed some degree of headache-related disability measured by the PedMIDAS scale. In a univariate analysis, headache was significantly more frequent in girls (35.1% vs. 25.5%, p < 0.001), teenagers with poor sleeping habits (36.6% vs. 27.6%, p < 0.001), lower physical activity (p = 0.002), those who did not have breakfast (37.3 vs. 28.4%, p = 0.001), smokers (10.5% vs. 4.9%, p < 0.001) and caffeine overusers (30.9% vs. 24.7%, p = 0.009). Comorbidities significantly associated with headache were: allergies (38.8% vs. 29.3%, p = 0.007), other chronic pain disorders (44.7% vs. 27.6% p < 0.001), mental health problems (53.2% vs. 29.0%, p < 0.001) and worse SDQ scores (p < 0.001). Conclusions: Headache is a common health problem among adolescents which impacts their quality of life. Headache is associated with presence of “unhealthy lifestyle” and other medical comorbidities. Educational initiatives should be started.