Well, some people will say, “the Virgin is weeping because of all the evil in the world, etc.” People take away different things from it. I can’t say that I know exactly what a weeping icon means, but I do think it is some kind of sign from God. Maybe one of the things God uses to get our attention. The ones I have seen I believe to be miracles (or “miraculous signs” as one priest puts it). I have seen the tears form and drip. I believe the phenomenon to be legitimate. I have been friends with the priest at St. Nicholas for over a quarter century, and I have been behind the iconostasis, and saw no way for the phenomenon to have been rigged, so I am assured no fraud has been committed. The tears are not just oil, nor are they a substance that could have oozed from the paint or wood. (There is a famous icon in Russia that produces myrrh.) My friend, the priest, told me that they had the tears analyzed by a university lab, and they were found to be some kind of living, organic, and replicating substance. (I had this conversation a long time ago, so I don’t remember if they said what it actually was.) There have been healings associated with the ill or infirm person being in the presence of the icon while it was weeping. A member of my church was being treated for leukemia and was weeks away from death. He was prayed for and anointed with the tears from the icon. When his doctors in the hospital checked him afterward, he was in complete remission. That was about 10 years ago, and he is still in the pink of health. He was told he could not or should not father children because of the treatments he had been given. Today he has two healthy young sons.
So that is my take on it. I believe in a God who can and does do miracles. If He chooses to act in this way, who am I to argue? Before I converted to the Orthodox Church, and before I had seen the icons with my own eyes, I would not have given them much thought. I might have even dismissed them. But when I think of the little miracles around me, of the other ways God gets my attention and reminds me of His reality, why would I dismiss something such as this? Christianity, especially its Orthodox form, is an incarnational faith. Orthodox believe that God uses the things of the physical world —water, bread, wine, oil, even wood and paint — to manifest spiritual realities. Why would it be such a leap to believe He would make an icon weep?
Just an interesting coincidence on the Chicago icons. The now-retired priest of St. Nicholas, Fr. Philip Koufos, has a brother, Fr. Theodore Koufos, who is a priest in Toronto. Both are iconographers. Fr. Theodore wrote (painted) the icon that wept at St. George.
Thank you for your reply.