@Jonathan Klemm- I have an empty lot next to my property. Fire occurred and nothing has been done to the property for several years. I searched online and saw taxes was up for tax sale. Unfortunately State of IL/ City of Chicago does not make it easy in terms of understanding the pitfalls. So far this is what I learned:
1) There will be time set by cook county tax sale to register for an upcoming sale. Usually its every 2 years.
2) You have to register. Meaning provide identification (Driver's license, etc.) & fund your account. If you don't do this before the deadline than you can not bid in the cook county tax certificates.
3) Once you are registered you can look at previous historical pricing of winning bids and property pins. You can bid 0% to 18% of the face value. Meaning if property taxes owed is 100 dollars and you bid 18%. You only have to pay 82 dollars. If the property taxes ever get redeemed you get paid 100 dollars plus appropriate interest. The current market is hot and most of the bids are at 0%.
4) Pitfall that I wish I had known- Past taxes. When you win the tax certificate you have to pay any back taxes. You have to order this from cook county. I won on a lot (cost approximately 1k), but it has over 40k worth of back taxes. Still learning. Messaged for any updates.