Moving to Chicago from Oakville ON

I have accepted a job offer in Chicago and will be relocating in Protected content (I told them I am not putting in my resignation until I have the TN Visa in hand). My wife and two girls (7, 10 yrs old) will follow once they are done with school.

So here are my questions:

1) Apart from Naperville (my new boss lives there) are there any other areas which are safe, have good schools and public transportation? He also mentioned Wheaton. I also like from what I found on the internet Skokie, Evanston, Wilmette. Any real estate agents you can recommend?

2) Is there any difficulties signing up your children in good public schools? Do all schools have before and after care?

3) My wife who has a background in Interior Design (a NAFTA profession) would like to look for work when things get settled. Any difficulty applying for a TN Visa within the US at US.

4) Any suggestions or tips would be appreciated. It's always nice to learn from other people's mistakes.

Thank you!