Background: Gallstone ileus is a rare cause of bowel obstruction, often presenting with nonspecific symptoms that delay diagnosis. This study assessed the diagnostic value of CT imaging and its correlation with histopathological findings in confirmed cases. Methods: A retrospective analysis of 14 patients with surgically confirmed gallstone ileus was performed. All underwent abdominal radiography, ultrasound, and CT. Imaging findings were evaluated for calcification type, impaction site, and fistula presence. Histopathology from surgical specimens was used for correlation. Relative risk (RR) and 95% confidence intervals (CIs) were calculated, with adjustments for small sample size. Results: Rim-calcified gallstones were the most common (50%) and significantly associated with chronic inflammation (RR 1.42, 95% CI: 1.05–1.93). Cholecystoduodenal fistulas were most frequent (57.1%), with a 92.8% imaging-pathology concordance. Ileal impaction (35.7%) was linked to increased risk of bowel necrosis (RR 2.0, 95% CI: 1.1–3.6). All stones were >3 cm; two patients had recurrence. No perioperative mortality occurred. Conclusions: CT imaging demonstrates high diagnostic accuracy and strong correlation with histopathological findings in gallstone ileus. Identifying calcification patterns and impaction sites aids early diagnosis and surgical planning.