Although the association of vitamin D levels with cardiovascular risk profiles among Hispanics/Latinos has been studied, little is known about this association among Hispanics/Latinos with chronic conditions. This pilot study determined serum vitamin D and parathyroid hormone (PTH) levels in a sample of participants from the University of Illinois at the Chicago Cohort of Patients, Family and Friends (UIC Cohort) and examined their association with traditional cardiovascular disease risk factors. From July 2012 to June 2016, the UIC Cohort study enrolled and conducted clinical examinations on men and women ages 18 years and older, who had one or more diagnosed chronic diseases/conditions (excluding cancer). This pilot study sample included 40 participants from the six main Hispanic/Latino background groups in the United States, namely Dominican, Cuban, Puerto Rican, Mexican, Central American, and South American, and were grouped by Caribbean or mainland origin. No substantial differences were noted in the vitamin D-related measures by Hispanic/Latino background, but the PTH levels were somewhat higher in the Caribbean vs. mainland group (43.0 ± 4.6 vs. 38.6 ± 2.7 pg/mL). The associations between selected CVD risk factors (systolic and diastolic blood pressure (SBP, DBP), total cholesterol, glucose) and PTH and vitamin D-related analytes were investigated using interval-censored multivariate regression models adjusted for age, sex, percent body fat, serum albumin/calcium, and Hispanic/Latino background. A negative association between total 25[OH]D and blood pressure was corroborated (SBP: β = −1.2, 95%CI = −2.0, −0.3; DBP: β = −0.7, 95% CI = −1.2, −0.1), whereas a positive association with total cholesterol was observed (β = 1.9, 95% CI = 0.02, 3.7). Levels of 1, 25[OH]2D were not associated with CVD risk factors, whereas 24, 25[OH]2D3 was associated with blood pressure (SBP: β = −13.0, 95% CI = −20.7, −5.2; DBP: β = −6.3, 95% CI = −11.6, −1.0). Estimated free 25[OH]D was inversely associated with both SBP (β = −3.5, 95% CI = −6.1, −0.9) and DBP (β = −2.1, 95% CI = −3.8, −0.3). Similarly, calculated bioavailable 25[OH]D was inversely associated with both SBP (β = −9.2, 95% CI = −15.9, −2.4) and DBP(β = −5.3, 95% CI = −9.8, −0.8). In conclusion, a negative association between 25[OH]D with BP was observed and a positive association with lipids is suggested. Due to the small sample size, most associations did not reach statistical significance.