If it looks like the courts will rule against against Illinois - it doesn't mean that everyone lines up and votes "Yes" for HB148. It also doesn't mean they rush and put in draconian laws designed to subvert the spirit of the ruling.
Illinois is not Chicago. Many times - and certainly on the gun issue, Chicago is politically monolithic. It is a machine with a driver at the wheel (at times). But the state of Illinois is not like that. So it's not as if the legislature - seeing that current IL law is going to be ruled unconstitutional - can just sit down in a session and create restrictive anit-gun laws that pass constitutional muster.
The difficulty will arise when alternates to 148 are proposed.
It no longer becomes a straight up or down vote. You have a a situation where a gun bill that allows cc is voted against by pro-gun politicians because it has provisions in it like "may issue". You also have a situation where politicians who are really anti-gun can can avoid getting branded as anti-2A in the eyes of the general public and can go on the radio and say "we voted for reasonable legislature that would allow Illinois citizens to carry a weapon for self-protection - but that was rejected."
All in all, it doesn't look good for anti-gun politicians in Illinois to be the last state in the entire union to not allow some for of carry. In a sense there is already a victory for gun rights advocates because it looks increasingly like we're heading toward the end-game of how the right to carry will be regulated, and that is a huge difference from the question of if Illinois citizens will be allowed to carry.