Background: Bladder cancer, specifically urothelial carcinoma (UC), poses a significant health concern in the United States and is significantly influenced by tobacco use. Despite its prevalence, routine UC screening is not recommended due to diagnostic limitations and uncertain benefits in long-term survival. Objective: This study examined the effectiveness of urine dipstick screening for UC in subjects already at elevated risk for UC due to substantial smoking histories, who were undergoing low-dose computed tomography (LDCT) for lung cancer screening. Methods: A prospective study was conducted at a single academic center to screen patients undergoing annual LDCT for lung cancer screening for UC. Urine dipstick tests were performed on patients without a history of gross hematuria or previously diagnosed as having UC. Statistical analyses were used to evaluate the relationship between smoking history, urinalysis results, and the prevalence of urological malignancies. Results: We enrolled 201 patients with a mean age of 64.4 years and a balanced gender distribution. Urine dipstick tests detected red blood cells (RBCs) in 15% of patients, with 2.1% showing microhematuria on formal urinalysis (>2 RBC/high power field). Nine (4.5%) participants were advised to undergo comprehensive hematuria evaluations. In addition, four (2%) participants had a history or were newly diagnosed with urological malignancies (three bladder cancer and one kidney cancer). Conclusion: Urine dipstick testing during lung cancer screenings in patients with significant smoking histories may facilitate early detection of urological malignancies, potentially improving patient outcomes. Further research is required to validate these findings, determine cost-effectiveness, and develop standardized screening strategies.