Karl I spoke to my wife Becky who's an Allstate Insurance agent. While not sure what the state laws are in Il. she did mention what kind of things they would be looking at in their "investigation" to see if he was insured. Most insurance has a grace period (Allstates in WA is 10 days). They will look to see if it was "terminated" or in a "cancel status" etc. One thing she did mention is that you could file under uninsured motorist on your own coverage (if you have that), although you will likely be paying your deductible for that. Good luck and there are a lot of variables that change by state.