This case presentation involves a 31-year-old pregnant woman (gravida 2, para 1) in her 33rd week of pregnancy, who presented to the Emergency Department of General Hospital of Trikala, in Greece, complaining of 24-hour abdominal pain, vomiting, and diarrheal stools. With a possible initial diagnosis of acute gastroenteritis, it was decided to admit the pregnant woman to the Obstetrics and Gynecology Department. Abdominal ultrasound revealed thickening of the gallbladder wall without the presence of gallstones or distension of the intrahepatic and extrahepatic bile ducts. Clinical examination by a surgical team, combined with ultrasound and laboratory findings, established the diagnosis of acute cholecystitis. After successful conservative antibiotic treatment, the patient was discharged from the department on the fifth day of hospitalization. She underwent laparoscopic cholecystectomy during the puerperal period. In this paper, after describing a case of acute cholecystitis in pregnancy, we highlight the significant diagnostic difficulties and therapeutic dilemmas regarding the management of these patients, including their reluctance to use invasive diagnostic methods and their concerns about the teratogenicity of administered drugs.