Hi R.,
I cannot offer advice about Jewish schools in the city since I am not familiar with them. What I can say is that unfortunately, the "northshore" gives Jews a bad rap. I believe it to be the area the kids grow up in vs being Jewish or not. And I do know what you are talking about the kids/families feeling they are "entitled" to certain things. Again, I feel it's the area, not being a Jew per se. I am a conservative Jew & grew up in Wheeling. I think it boils down to where you live & how you are raised. I worked for everything & was never handed things on "silver platter" never feeling I was automatically entitled to anything. I am pregnant with my 1st child & live in Gurnee. We are looking for a sense of Judiasm up here - temple, people, etc. But it's a slow growing Jewish community up here. Anyway, sorry for the rambling...just my two cents worth. Good luck in finding the school that meets your needs.