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1) Salary is on CPS website; general living expenses in Chicago are often discussed on the site in this thread. Generally pay is OK, and you can live decently as a single, but supporting a family on a CPS salary without a working spouse is a stretch.
2) No. You get hired. If they like you, you get to come back. If you do that three years in a row it is called tenure, but CPS flushes more than its fair share of tenured teachers out...
3) You are kidding. While there are ways to get reduced tuition and free courses toward advanced degrees the CPS is not known to do much to help out those who still have students loans to pay off. Probably a good thing, given the level of corruption that Illinois is known for.
4) Mostly. Any reasonably normal college transcript will eventually work its way through the Byzantine systems of state evaluators that should be grant you the same certificate you earned where you live. Maybe even certify you for a heck of a lot more course than you want to teach... It might take a while and you may have to work without a valid certificate, which may effect your pay (imagine that). You will probably have to do something inane, like a pass a "test" that proves you can read and write English or some other language, take an even sillier "test" about the Illinois Constitution, even though they won't actually give you a copy of the Document, instead selling you a "test prep booklet" that has the exact questions to memorize. And they make everybody take a class on "Educating Special Needs Students in The Least Restrictive Envirornment"...
5) ALL OVER THE MAP -- there ARE Universities and Foundations that help, even the Union and the Board of Ed have some initiatives, but some individual schools have NO ONE that understand how this is supposed to work and others are on top of it. Totally hit or miss...
There might be some blogs with more details, but nothing too detailed, official or too widely updated. Mayor gets enough bad press...
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