We are in our 4th year of homeschooling our now 10 year old daughter and absolutely love it! Our choice to homeschool came out of very disappointing experiences we had with 2 well-known, expensive private school in Chicago. We just became so dismayed with the level of education she was getting for the amount of money we were spending that we couldn't justify it any longer.
My husband and I have our own business so are able to be somewhat flexible to accomodate the homeschooling - we both work with her so it doesn't fall completely on one of us. Having said that, however, because we do have to tend to the business, we decided to use a homeschooling program called "K12" - http://www.k12.com (it is a fully accredited homeschooling program). This program has the curriculum for each level - kindergarten through 12th grade already planned for you. You purchase the books and other learning materials and access to the website - for our daughter it costs about $1,000 a year. It depends on how many classes you sign up for - she is taking a full load - math, literature, grammar and spelling, art, history and science. Also, what is nice is that you can do classes at different levels. My daughter is very advanced for her age in math and literature so is taking a higher class level, whereas, with history and science we decided to have her take her class level because she had gotten so little of those subjects in private school. They also furnish teacher guides and the answers to all the tests. Some of the lessons - especially in science are done online - which I find my daughter really enjoys. Anyway, K12 has been very valuable to us because we don't have to spend a lot of time working out a curriculum and schedule ourselves -plus we find that it is very thorough and our daughter is learning so much more than if she were in a public or private school. And so are her parents! It is really a lot of fun!
We also do supplemental things with her which may or may not tie in with her K12 schedule. If it is a beautiful day, we may just take the day off from her regular schedule and go to the Chicago Botanic Gardens to walk and sketch whatever we see - or maybe go to a museum - or build a snowman! It is just so nice to be able to that together - and not worry about her missing a day of school!
We have not yet been involved in any homeschooling groups but we do subscribe to "Home School Legal Defense Association" -
www.hslda.org. They keep us updated on any legal issues in Illinois plus their website has all sorts of information for homeschoolers. I'm not sure where you are in the city, but one homeschooler group I have heard a lot about is the Evanston Homeschoolers (not sure of exact name but I'm sure you can find their website).
You do not have to register in Illinois as a homeschooler. Also - you can be eligible for teacher specials and credits at many stores (for school supplies, books, craft stuff, etc.) - just make sure you tell them that you homeschool.
I wish you much luck in your new venture!