For digital support services to become part of care systems, it is necessary to understand their affordability and perceived value by caregivers. Considering the substantial information needs experienced by informal caregivers, the increased availability of digital support services for caregivers as well as the potential they offer, further understanding of caregivers’ willingness to pay for digital support services is needed. Objective: The aim of this study is to identify associations between informal caregiver’s characteristics and their willingness to pay for digital support services in two countries: Italy and Sweden. Methods: A sample of 378 respondents participated in a cross-sectional survey by completing the online questionnaire. Respondents were recruited by the Italian National Institute of Health and Science on Aging and the Swedish Family Care Competence Center. A two-part regression model was used to investigate the association between willingness to pay and the independent variables and to determine the adjusted mean willingness to pay. Results: Caregiver’s gender, care recipient relationship to the caregiver, care duration, the total household income and the amount spent per month on professional caregiving service are all associated with willingness to pay. Conclusions: It is widely acknowledged that caregivers are a group with high levels of unmet needs when it comes to their access to information and other services. Factors such as demographics, socioeconomic resources and the caregiving context may play a role in caregivers’ willingness to pay for digital support services. Future research that evaluates the cost-effectiveness of digital support services is needed in a context of a growing number of informal caregivers and ever scarcer resources.