Phlebectasia is a rare condition that refers to the dilatation of any vein in the neck. It is more common in the internal jugular vein and in boys. Diagnosis of the condition is based on ultrasound with Doppler and contrast-enhanced computed tomography. Management of this condition is conservative unless there are complications that may require surgery. Here, we present two pediatric cases of internal jugular phlebectasia. The first patient was an 8-year-old boy, and the second was a 5-year-old boy. They both presented to our clinic with recurrent tonsillitis for tonsillectomy, and both were incidental findings.