"BeginningJune 1st, 2008, Illinois requires a permit for all direct-to-consumer wine shipments to the state. A winery must receive the permit before it may begin/resume shipment to the state. In 10 days, under the newly-promulgated wine shipping law, wineries and retailers that have been shipping to Illinois under a reciprocal agreement will no longer be able to ship to the state without a permit. The Illinois Liquor Control Commission has not given any indication of a grace period for shipping while applications are in process"(cited from http://shipcompliantblog.com/ )
What does this mean? Well when I was in Santa Ynez and Paso Robles this past January several wineries told me (smaller ones) that they would not be shipping any more to Illinois customers. A cool wine shop in the Seattle market shared that it didn't make sense for me to be on their mailing list because of this law.
While other states seem to be loosening up their laws in this area, Illinois continues to have its strings pulled by liquor distributors including the largest one who owns the Chicago Blackhawks.
Don't get me wrong, I support quality wine shops here in the Chicago area as well..but they are hard pressed to carry the variety of wines available either directly from a niche winery or internet site