Second, yes there are many chips which are known or believed to have been used in Chicago area mob-run illegal casinos. Check out this link to see illegal gambling operation chips from Illinois: http://chipster.net/guide/ILLINOIS.pdf
I'm not sure how up-to-date it is anymore, but it's a fantastic start. Also, you can peruse record of some of the chip manufacturers and distributors including some that are from the Chicago area: http://www.preservinggaminghistory.com/ One of the companies at least, Taylor, was mob-owned. There are some real experts about the Chicago area in particular. I'm not one of them, but I really enjoy their posts. I'm sure Gene Trimble can tell you a number of people (including him) who know a lot about mob-run casinos around Chicago. Of course, they were all over the country (and even around various parts of the world), but you will find no lack of chips from Illinois.
My advice, collect what interests you. If you decide to branch out, great. If not, specializing is fun, too. It's easier to learn the background for specific collecting areas than it is to learn everything. And as Gene says, the history is the best part. Otherwise they are just clay disks. Or something like that.
Above all, don't be afraid to ask anything on the board. It's really one of the best ways to learn.
And have fun.
Michael Siskin
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