I don't think they necessarily "need" to win. After all, there's no guarantee the Courts will force a shall-issue or OC or anything remotely desireable.
What this does do is give political cover and economic ammo to the 5 or 6 remaining votes necessary to pass the shall-issue bill which is still alive in the Legislature.
Daley et al can fume all they want but in these times, with even the anti's paying lip service to fiscal responsibility, the pro-carry folks simply have to start listing the costs involved with suits and appeals.
That may be enough for some fence-sitters to shake their heads and vote "aye" on grounds of "fiscal responsibility".
Anyway, if I were in the Illinois carry movement that's what I'd be pushing rather than wait and hope for some judge-made law that will please no one a couple years worth of appeals down the road.
They have a great bill as it stands, they can't do much better and it is not realistic they'd get "Vermont-carry" (which would still leave them without reciprocity with many states).
They need to use the suits as a stick, not a goal.