Yes, I graduated in 99. I know a lot of people who teach for CPS and work at many levels there. There are still good schools.
Well, the middle schools may still be a little lacking. There are definitely good elementary schools and high schools.
I am a pretty firm believer that at least 50% of what a child get's out of an education is what they put into it and a lot of that comes from the parents attitude.
You're a little foolish is you think the violence or drugs will be any better or worse at a good CPS compared to most private schools or schools in the burbs.
I'm not saying things won't be a little better at a private school, or in the burbs. Or it might not be a little easier sometimes. But with a little insight and if you're kid is motivated you can find a really good education in a CPS. It's not 100% necessary to go to private schools.
I'd put my education at my high school up against any school in they city.