If you're in northern Illinois, than This tree is not likely to be shortleaf pine (Pinus echinata) if you're located in northern Illinois. My guess is that this tree is likely an Austrian pine (P. nigra).
Attempting to diagnose general tree decline problems over the Web is generally not very productive. Therefore, I would strongly encourage you to contact a certified arborist for an on-site assessment of this tree.
List of Certified Arborists in IL: