You cannot sell a weapon to a resident of another state unless you have an FFL.
Most Indiana FFLs will not sell to an Illinois resident because if they do not precisely follow Illinois state and local laws their license and freedom is at jeopardy.
IF you are going to effect a transfer mail it to an Illinois FFL.
If for some reason your friend cannot take delivery of the weapon, the FFL make keep and sell it without any compensation back to you.
If it were me I would explain to my friend that I can't do the deal. Too many bad things happen mixing guns, Illinois, and Chicago in the same drink.
I have someone who is interested in buying a handgun from me who lives in Illinois. From what I've read in this thread is that the handgun needs to be delivered to a FFL dealer who resides in IL. and that person pass NICS and whatever other IL laws that are in place before that person can take possesion of that handgun. But I could still sell it to him. The handgun just has to transfer through a IL FFL dealer. Right?
Would my selling this handgun and taking delivery of payment before the handgun is legally transferred illegal?