The aims of this cross-sectional survey were to evaluate the knowledge, attitudes, and self-reported adherence to recommended vaccinations among a random sample of patients with chronic conditions presenting for a medical visit in out-patient clinics in Italy. Patients who were healthcare workers (HCWs), those with diabetes, those who had received information by Internet, physicians, and friends/relatives, and those who needed more information were more likely to know that the influenza vaccine is recommended for patients with chronic diseases. More than half (58.2%) and 8.9% self-reported to have received at least one recommended vaccination and more than one, respectively. Patients who believed that vaccine-preventable diseases (VPDs) were dangerous for them, those who had received information by physicians, and those who needed information were more likely to have received at least one recommended vaccination. This behavior was less likely in married patients, those who were worried about the side effects of the vaccines, and those who suffered from renal failure. The results highlight the need to implement effective vaccination programs in order to decrease the complication of VPDs in at-risk population.