To test the association between sleeping problems and multiple epidemiological factors among women over 50 with a chronic condition. Method: The Medical Outcomes Study Sleep Scale (MOS-SS) was employed to measure sleep problems among 1,925 participants with chronic conditions who also responded to questions about health service use, self-care and demographics. Results: About 43% of women reported sleeping problems. Women were more likely to have a sleeping problem if they reported some difficulties with available income, odds ratio (OR) = 1.61; 95% confidence interval (CI): [1.27, 2.04]; p < .005, or were struggling with available income (OR = 2.84; 95% CI: [2.04, 3.96]; p < .005). Women were less likely to have sleeping problems if they were highly physically active (OR = .63; 95% CI: [0.51, 0.79]; p < .005). Discussion: Medical professionals should be aware of the significant risk of sleeping problems among mid-age and older women with chronic health conditions, particularly those who have financial concerns, are sedentary, or are not highly physically active.