Off Topic? Hardly. These are just the sort of questions that the layman needs to know the answers of.
Should Kachalsky not be granted cert (in which case, neither would Woollard be granted cert), then there would be no need for Madigan to file for a petition of cert. The State could then go ahead and pass a carry law similar to NY/MD, with no ill effect from an immediate adverse ruling at the district or circuit levels.
Of course, if cert is granted, then IL's position becomes somewhat problematic.