Background An increasing number of retirees continue to work beyond retirement despite being eligible to retire. As the prevalence of chronic disease increases with age, working beyond retirement may go along with having a chronic disease. Working beyond retirement may be different for retirees with and without chronic disease. We aim to investigate whether demographic, socioeconomic and work characteristics, health and social factors predict working beyond retirement, in workers with and without a chronic disease. Methods Employees aged 56–64 years were selected from the Study on Transitions in Employment, Ability and Motivation (N = 1125). Questionnaire data on demographic and work characteristics, health, social factors, and working beyond retirement were linked to registry data from Statistics Netherlands on socioeconomic characteristics. Separate prediction models were built for retirees with and without chronic disease using multivariate logistic regression analyses. Results Workers without chronic disease were more likely to work beyond retirement compared to workers with chronic disease (27% vs 23%). In retirees with chronic disease, work and health factors predicted working beyond retirement, while in retirees without a chronic disease, work, health and social factors predicted working beyond retirement. In the final model for workers with chronic disease, healthcare work, better physical health, higher body height, lower physical load and no permanent contract were positively predictive of working beyond retirement. In the final model for workers without chronic disease, feeling full of life and being intensively physically active for > = 2 days per week were positively predictive of working beyond retirement; while manual labor, better recovery, and a partner who did not support working until the statutory retirement age, were negatively predictive of working beyond retirement. Conclusions Work and health factors independently predicted working beyond retirement in workers with and without chronic disease, whereas social factors only did so among workers without chronic disease. Demographic and socioeconomic characteristics did not independently contribute to prediction of working beyond retirement in any group. As prediction of working beyond retirement was more difficult among workers with a chronic disease, future research is needed in this group.