shipping wine out of Chicago -- anyone know of a shipper?
That depends a lot of what state you are shipping to. All the states have different laws. I'm not sure a shipper with a license exists. You would probably have to find a retailer or wholesaler (perhaps even a winery but they are almost surely limited to their own wines) who has the license and is willing to help. Even then, I don't know enough about Illinois laws to give you good advice.
Out of date laws force law-abiding people to ship "olive oil", "grape juice", "food stuffs", and the like. Some people have even recommended stuffing newspaper in the foam shipper around the tops of the bottles to keep the bottles from rattling.