1. Did you take a security deposit? If the answer is yes you do NOT want to evict unless you are confident your security deposit game is perfect. In evictions the tenant rights attorneys ask prospective clients one question: did your landlord take a security deposit? If the answer is yes, they will take the case. If the answer is no, they will typically refuse to take the case.
2. I would meet with him and bring a "cash for keys" agreement. I would also bring any notices required by Chicago or Illinois for eviction to move forward (mediation thing, etc.). But cash for keys is great because it provides the carrot and the stick. Carrot -- take my $500 and leave. Stick: eviction. If you bring both and serve the pre-eviction stuff it makes it more clear that you will evict.
This is where you need to talk to your eviction attorney NOW not later after you've already screwed it up and wasted time.
3. If you don't have an attorney for your eviction I would retain this guy now to get your advice on exactly how to move forward and what notices are required, etc. But I think knowing how backed up Cook County is and how slow the process is moving (all cases go to one court like a central station) I would do anything I could to avoid eviction including cash for keys. Maybe you pay him $500 to get out. Find out what the attorney will charge and offer the tenant some amount of that.
His name is Rich Magnone and he knows his stuff. This is his highly informative blog:
https://www.chicagoeviction.co...