Pediatric vomiting and feeding difficulties are common presentations in both emergency and outpatient settings. Although these symptoms are often attributed to benign causes such as infections or gastroenteritis, structural and functional esophageal disorders must also be considered. This report describes two diagnostically challenging cases of esophageal obstruction in children. The first involves a 10-year-old boy with Angelman syndrome, ultimately diagnosed with a double aortic arch causing extrinsic esophageal compression. The second case features a previously healthy 13-year-old with chronic vomiting, later identified as having primary achalasia. These cases highlight the importance of maintaining a broad differential diagnosis and employing targeted imaging to prevent delays in diagnosis.