Objectives: An increased burden of chronic diseases in the working age population is observed across high income countries. Persons with chronic diseases (PwCDs) are less likely to maintain or return to work due to several constraints they experience. The purpose of the study was to assess the preferences and needs of PwCDs regarding 6 areas of flexibility at the workplace. It was assessed whether there were any personal characteristics associated with higher or lower expectations and needs. Material and Methods: This was a part of a large multicenter international project, i.e., the PArticipation To Healthy Workplaces And inclusive Strategies in the Work Sector (PATHWAYS) project, aimed to contribute to the development of innovative approaches to promote professional integration and reintegration of PwCDs into the work sector. In Poland, 59 respondents diagnosed with different chronic diseases were identified through advocacy groups. An on-line survey was conducted to collect information on their needs and expectations. A cluster analysis was performed to reveal some expectation types which differentiated individuals across 6 analyzed domains, along with a multivariable logistic regression to identify some characteristics associated with a special expectation type. Results: Workplace facilitator items were generally scored as needed (“rather conductive” and “very conductive” groups identified). The factors positively associated with higher needs in this domain were education, and a hindering type of the disease. Unrestricted working hours were very conductive or indifferent, and were positively associated with education. Legal solutions were more conductive for older people. Medical support, access to training, and supervisors’ knowledge were needed in general, with no associations with the personal characteristics identified. Conclusions: Persons with chronic diseases report several facilitators which are needed for them to maintain or return to work, but they are not satisfied with the existing economy in Poland. These needs should be taken into consideration in the effective policy development. Int J Occup Med Environ Health. 2020;33(4):427–44