I know where you are at! I just weaned my 2 1/2 year old from his bottle. I have two other children who are 9 and 7. The first one was the same as yours. Ear infections left and right and would not dream of going to bed without a bottle. He had tubes in his ears because of the infections. And yes, that did help, but I look back on it now and see that it really wasn't necessary. He was going to grow out of the infections at one point or another. He was 8 months old when we had them put in. I actually weaned him to a cup about the age of 2. He started taking that to bed until he was 3. I eventually just sat it in his bed and told him it is there just in case he got thirsty. And that is how he was weaned. My second child just said she didn't want her bottle anymore and threw it in the garbage! ha ha! Of course that didn't stop the tears at night.... My third one has another lovey, which is his favorite soft blankie. He is like the little dude from Snoopy.
I know none of that was a big help. But I am here to say keeping my children on the bottle did not cause tooth decay. They are not sitting in class right now with bottles attached to their mouths. I just really think getting children off the bottle before they are ready is such a wrong thing. The bottle is their comfort at night. Much like a night light.
If he can understand some things you say, try to explain to him the bottle is not for big boys and that he is a big boy now. Try on the weekends to put him to bed at nap without his bottle (or whenever you are home together). Don't let him cry it out. That is just cruel. Talk to him softly and be patient. Rub his back and sing him songs. Let him pick out a teddy bear that he can sleep with so that can be his comfort. I won't lie and say it will be easy. Just take your time and don't lose your cool in the process.