Chiari Type I malformation is characterized by cerebellar tonsil herniation through the foramen magnum. Manifestations may include new-onset upper airway obstruction. We describe two patients who had bilateral vocal cord paralysis and Chiari Type I malformation. These cases highlight the importance of suspecting a neurologic abnormality such as Chiari malformation in new-onset upper airway obstruction and/or bilateral vocal cord paralysis in adolescents in the absence of an obstructive lesion, though the development of cranial neuropathies or radiographic evidence may be delayed. Establishing a proper diagnosis is critical as Chiari I malformation can be treated with neurosurgical decompression, with possible improvement.