Objective: This article addresses the association between course of chronic disease and lifestyle. Method: We examined differences in unhealthy lifestyles - smoking, excessive alcohol use, being sedentary - and transitions herein after 6 years in prevalent and incident chronic disease categories - lung and cardiovascular disease, diabetes, and osteoarthritis and/or rheumatic arthritis - among 2,184 respondents aged 55 years and older from the Netherlands. We also examined if transitions in lifestyle co-occurred with changes in disease-related symptomatology. Results: Proportions of respondents who smoked decreased over time, whereas proportions of respondents who were sedentary increased. Respondents with incident cardiovascular disease demonstrated more lifestyle transitions than respondents from other disease categories. Respondents demonstrating healthy lifestyle transitions did not differ from those persisting in unhealthy lifestyles in change in disease-related symptoms. Discussion: Health promotion may benefit from these findings in a way that patient groups at risk for not initiating healthy lifestyles might be identified sooner.