On February 24, 2010, about 1020 central standard time, a Bombardier Inc. BD-100-1A10, N515FX, piloted by two airline transport pilots, sustained substantial damage when a deicing vehicle impacted the airplane during deicing operations prior to an intended departure from the Chicago Executive Airport, near Wheeling, Illinois. Both pilots and both deicing ground crewmembers were uninjured. The fractional ownership flight was conducted under the provisions of Title 14 Code of Federal Regulations Part 91, Subpart K. Marginal visual meteorological conditions prevailed at the time of the accident and an instrument flight rules flight plan was on file. The positioning flight was destined for the Chicago Midway International Airport, Chicago, Illinois. An airport maintenance person stated he saw a Signature de-ice truck hit the horizontal stab on the right hand side (as sitting in plane). The Signature de-ice truck boom hit the tail, not the operator cab (where the de-ice operator stands). He said he saw the nose of the plane move forward, then down, and "I figured that the plane was hit." The pilot then came out of the aircraft to inspect it with Signature personnel. According to the pilot’s accident report, the deicing operation took place following their taxi to a run up pad near runway 34 and taxiway kilo. The fixed base operator’s [FBO] deicing/anti-icing training guidebook, under Equipment Operation, states that the deicing vehicle driver should “always know where the boom and bucket are located.” There were supervisors at the airport during the deicing operation. There was no supervisor overseeing the deicing operation. The FBO’s training guidebook did not require that a supervisor oversee deicing operations.