I would not fly. I have similar issues, once I was half deaf for a week, other times I have been in dreadful pain when I was having sinus and ear issues. I would say based on my experience the ear planes would not for the situation you are in now, they did not for me when my ears were already messed up I finally went on a year round once a day allergy tablet. About two hours before I fly I take pseudoephedrine, the kind you have to sign for at the pharmacy in Texas, I stay hydrated and now I never forget my ear planes or Flents Flite Mate ear pressure reducing plugs.