Falls are an important health concern among older adults due to age-related changes in the body. Having a medical history of chronic health condition may pose even higher risk of falling. Only few studies have assessed a number of chronic health conditions as risk factor for falls over a large nationally representative sample of US older adults. In this study, Behavioral Risk Factor Surveillance System (BRFSS) 2014 participants aged 65 years and older (n = 159,336) were evaluated. It was found that 29.7% (n = 44,550) of the sample experienced at least one fall and 16.3% (n = 20,444) experienced more than one fall in the past 12 months. According to the study findings, having a medical history of stroke, CKD, arthritis, depression, and diabetes independently predict the risk of first-time falling as well as the risk of recurrent falling in older adult population while controlling for other factors. On the other hand, having a medical history of the heart attack, angina, asthma, and COPD did not predict the risk of first-time falling, but did predict the risk of recurrent falling after experiencing the first fall in this population.