Background: Chronic appendicitis is a condition unfamiliar to many physicians and is often referred to as a controversial diagnosis. This can give rise to diagnostic delay. Case presentation: We present two cases of chronic appendicitis: a Caucasian female aged 21 years and a Caucasian male aged 34 years. The patients had different clinical presentations, which led the initial investigations in very different directions—tropical infectious disease and possible malignancy, respectively. In both cases, radiological imaging was the key investigation leading to the final surprising diagnosis. Conclusion: With these two case stories, we wish to draw attention to chronic appendicitis as a possible differential diagnosis in younger patients with chronic or recurrent abdominal pain, particularly if the pain is located in the lower abdomen and is accompanied by fever.