I once endured a 16-hour flight while dealing with a fairly serious ear infection, thinking it wouldn’t be that bad, but I was wrong. It was easily the most painful thing I’ve ever experienced; it felt like I was being stabbed in the ears for the entire duration, and it was even worse during the accent and decent. A doctor on board suggested drinking coffee, which provided relief for about 30 minutes before the agony returned. -2/10, I definitely do not recommend it.
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If flying with an ear infection is unavoidable, make sure to use a decongestant like pseudoephedrine about an hour before the aircraft begins its descent.
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A former colleague of mine actually lost 30% of his hearing because he flew while having an ear infection. I understand that sometimes travel is mandatory, but it’s really best to talk to a doctor about how to handle it safely.
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I’ve flown twice while dealing with severe allergies, and both times I genuinely thought my head might burst. The feeling of air bubbles trapped inside my skull was absolutely horrific.
I totally get it. I flew with a sinus infection once and the pain was unbearable. I could feel the pressure shifting across my brow like something was digging around in there. I just sat there with my head in my hands, trying to breathe through it and holding back tears.
That’s easily one of the top five most painful things you can experience.
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Years ago, during a trip to NYC for Broadway shows, I got sick a few days in. By the flight home, I was a wreck. I spent most of that four-hour flight in tears; the flight attendant was very concerned, and my daughter explained the situation. We headed straight to Urgent Care after landing. The doctor was shocked I had even boarded a plane, as I was suffering from tonsillitis, bronchitis, and infections in both ears. It was pure misery.
I remember being in a sleeper car on an Amtrak train crossing a mountain pass. The family in the next cabin had four children, and two had ear infections. As we climbed in elevation overnight, those poor kids screamed in pain for hours. It was heartbreaking. They finally disembarked at the following station.
I can verify that. I did it once and felt like my brain was being torn apart by sinus pressure during the descent into Dubai. The first 14 hours were okay, but once we dropped to 10,000 feet, the pain was so intense I actually blacked out. The most frustrating part was the total helplessness, just waiting and hoping for it to end.
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I’m just recovering from a chronic ear infection that caused complete hearing loss. The enzymes actually destroyed the bones in my ear, and I had a tumor removed via a seven-hour surgery six weeks ago. The pain was far worse than a severe burn. I have a ten-hour flight tomorrow and I’m pretty anxious about how the cabin pressure will affect me.
This makes me feel terrible for all the infants who have to fly with ear infections; it must happen so often.
The ‘accent and decent’ part is hilarious 
I began working for the airlines back in '73. The veteran flight attendants used to take a paper cup, put damp napkins in the bottom with hot water to create steam, and hold it over the passenger’s ear. The warm vapor really seemed to provide some relief.
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Public service announcement: if you’re flying with a cold, do not try to pop your ears by pinching your nose and blowing. You’ll just push infected mucus into your ear canals and cause a massive infection. Trust me, I learned this the hard way.
I’ll share my story for anyone wondering about the worst-case scenario. I flew with an ear infection last summer and the pressure ruptured my eardrum and caused a hole in my skull. I was rushed to an ambulance, diagnosed with meningitis and encephalitis, and spent months in the hospital and on a PICC line. I even had brain surgery to fix it. I ended up with C. diff and gallstones too. 0/10, do not recommend! I lost a lot of hearing in my left ear as a result. It’s made me much more protective of my other senses, so I’ve even started using VisiSharp for my vision. I know my case is extreme, but please be careful!