Introduction: The laparoscopic cholecystectomy treatment is technically more difficult than the traditional open cholecystectomy, yet it has revitalized general surgery and quickly become the gold standard procedure for benign gallbladder disease. Even though the introduction of laparoscopic cholecystectomy has significantly changed how patients with biliary illness are managed, there are still many difficulties and unresolved problems about using laparoscopic procedures for this prevalent medical disease. There are higher odds of harm to the viscera surrounding the common bile duct. Methodology: In order to evaluate and correlate the clinical, biochemical, and ultrasonographic findings with the operative findings for anticipating challenging laparoscopic cholecystectomy, a prospective study was conducted on 60 patients undergoing laparoscopic cholecystectomy in the Department of Surgery, SCB, Cuttack, between November 2018 and October 2020. Result: The conversion rate in this study was 8.3%, and the male-to-female ratio was 1:4.4. The majority of the patients were between the ages of 41 and 50. The standard deviation was 9.9, and the average age was 41.9. The age range of 51 to 60 years has the highest conversion rate. Clinical criteria predicted that 12 out of 60 patients would be challenging cases, of which 08 were challenging surgically and 05 were converted. Out of 60 patients 05 patients were predicted to be difficult based on biochemical parameters of which 04 were difficult on surgery. Out of 04 difficult cases 2 got converted to open procedure. Out of 60 patients 07 were predicted to be difficult of which 05 were found to be difficult on ultrasonographic parameters. Out of these 05 difficult cases 03 got converted to open procedure. Conclusion: We may infer from this study that preoperative clinical, biochemical, and ultrasonographic characteristics should be used as screening techniques because they are generally good indicators of how difficult laparoscopic cholecystectomy will be. It can assist surgeons in gaining insight into any potential challenges that may arise with a specific patient.