Chronic calculous cholecystitis may progress to rare complications, including contained perforation and inflammatory extension to the abdominal wall. We report the case of a 59-year-old woman with hypertension and diabetes mellitus presenting with right upper quadrant pain, abdominal swelling, nausea, vomiting, fever, and weight loss for three months. Computed tomography demonstrated diffuse gallbladder wall thickening, intraluminal gallstones, and a loculated collection extending to the abdominal wall and subcutaneous tissue, consistent with a complicated pericholecystic abscess. The patient underwent laparoscopic fenestrating subtotal cholecystectomy associated with drainage of the purulent collection. Intraoperatively, an intense inflammatory process and multiple adhesions were observed, preventing achievement of the critical view of safety. Frozen section analysis showed no evidence of malignancy. This case highlights a rare presentation of chronic cholecystitis and reinforces the importance of clinicoradiological correlation and individualized surgical management in complex cases with significant anatomical distortion.