It sounds like your plan to see an ENT specialist is a good one, as there are many possible causes of your symptoms.
Definitely eustachian tube dysfunction, where the tubes draining your middle ear down into the back of your throat do not function properly is a possibility. This would cause a "plugged up" feeling in the ears as well as a pressure feeling. Eustachian tube dysfunction would also be more common in someone with your history of multiple ear infections, which could have caused scarring of the middle ear or tubes.
Another possibility is a build up of wax inside the outer ear canal. This can definitely be severe enough to cause trouble hearing, and it also very commonly causes an "itchy" sensation inside the ear canal.
It is unlikely that your eye infection
issue is related to you plugged up ears. However, when you go to see your doctors
">doctor make sure to mention the eye issue to them as well, as I am sure they will be happy to take a look at that in addition to investigating your ears.
Based on what the ENT doctor finds, they will be able to recommend the appropriate treatment. For example, eustachian tube dysfunction can sometimes be improved with medications, and ear wax buildup can be removed in the doctor's office. Good luck!