So what did you decide? Where are you hunting? Plenty of trophies get taken in the otherr 101 counties of Illinois and there is a decent amount of public land scattered. Like everywhere else you have to walk farther than other hunters are willing to walk to get to the best spots. You can also take out adds on CraigsList and such to try and get permissions on private land.
I grew up hunting in Hamilton County on private land, lost it about 10 years ago due to sales and such. I hunted a few years in Johnson County near Shawnee and lost that due to a divorce/sale/lease. I am down to my own 12 3/4 acres in Champaign County now, had a huge construction project on it last year and traffic has yet to improve but there are some deer on it. With 8 months of "living" here you could apply for an IL License and such and get resident status, I believe 6 months gets you enough time for resident status.
Oh, and chicago bites, get out of there any time you can, there is a giant state here with a ton to offer outside of that cess pool.