Contractor suggests caulking cracks in chimney, is that the right solution?
This is the same question you asked a couple of days ago. BTW, NEVER use silicone caulk on chimney masonry cracks, especially if the crack passes through. There are special masonry high temp caulks for this purpose. In your case where water is passing completely through the brick joints, you really need to have it repointed.  Any competent contractor would not suggest silicone in this case. Find a new contractor.