Adolescents reporting persistent chronic illness at ages 16, 22, and 32 years (n = 296, limiting in daily life n = 52, non-limiting n = 244) were compared with those without any chronic illness (n = 401) in their life situation, psychosocial well-being and health habits at age 32 years. The data were drawn from a follow-up survey of a Finnish urban age cohort from age 16 until age 32 years. The group of persistent chronic illnesses included allergies (n = 249, 84%), non-allergic skin conditions (n = 10), migraine (n = 29), diabetes mellitus (n = 5), and others (n = 9). Results indicated that adults with persistent chronic illness limiting their daily life reported more depression and lower self-esteem than those with non-limiting chronic illness or healthy controls. Daily smoking was more common among females with any chronic illness than among healthy controls. No significant differences were found between adults with any persistent chronic illness (mainly non-severe allergic conditions) and healthy controls in psychosocial well-being. More attention in health care should be paid to psychological well-being in persons with limiting chronic illness. The study also raises the question how to improve health habit counselling within health care among females with chronic illness.