Carotid artery dissection causes 2.5% of ischemic acute strokes and is more common in younger rather than older patients. Extracranial lesions often manifest as transient and reversible neurological deficits until a stroke occurs. In this case, we describe a 60-year-old male patient with no known cardiovascular risk factors who experienced three transient ischemic attacks (TIAs) in four days while traveling in Portugal. At the emergency department, he was treated for an occipital headache associated with nausea and two episodes of decreased left upper-limb muscle strength lasting two to three minutes with spontaneous recovery. He requested discharge against medical advice so that he could travel home. During the return flight, he had a severe right parietal headache followed by decreased muscle strength in the left arm. After an emergency landing in Lisbon, he was referred to the local emergency department, where his neurological examination revealed preferential gaze to the right exceeding the midline, left homonymous hemianopsia, minor left central facial paresis, and spastic left brachial paresis. On the National Institutes of Health Stroke Scale, he scored 7. A head CT was performed, showing no acute vascular lesions (i.e., Alberta Stroke Program Early CT Score of 10). However, an image compatible with dissection was identified on CT angiography of the head and neck and confirmed by digital subtraction angiography. The patient underwent balloon angioplasty and placement of three stents in the right internal carotid artery with vascular permeabilization. This case highlights how prolonged and incorrect cervical posture and microtrauma secondary to aircraft turbulence may be associated with carotid artery dissection in predisposed individuals. The Aerospace Medical Association guidelines advocate that patients with a recent acute neurological event should avoid air travel until clinical stability is assured. As TIA is considered a harbinger of stroke, patients should be properly evaluated and avoid air travel for at least two days after the event.