We know little about the retirement plans of adults with chronic diseases. This research recruited Canadian workers 50–67 years of age from a national panel of 80,000 individuals (arthritis, n = 631; diabetes, n = 286; both arthritis and diabetes, n = 111; no chronic disabling conditions, n = 538). A cross-sectional survey asked participants about their expected age of retirement, future work plans, whether they were retiring sooner than planned, and bridged retirement. Chi-square analyses, analyses of variance, and regression analyses examined expectations and factors associated with them. Despite health difficulties, workers with arthritis and diabetes had retirement plans similar to those of healthy controls and consistent with normative expectations of working to a traditional retirement age. However, more respondents with arthritis or diabetes reported bridged retirement than healthy controls. Contrary to predictions, health factors accounted for less of the variance in retirement expectations than other factors. These findings point to the complexity surrounding retirement expectations and highlight person–job fit rather than disease factors alone.