If you attempt to go to court, the 30 days repayment is most likely what the judge will grant in my experience. 

Either way, he knows how both city governments and the courts work.

Quote from @Travis Timmons: @Xavien Rafael I don't doubt that you know what you are doing, but that is WAY too complex for a beginner.Just buy a property that you like with a well researched strategy in mind.

Chicago is a tenant friendly city and it takes months of court dates to get them officially evicted.

In the past 3 months, I have been getting calls from several investors interested in apartment complexes.

If they don't than I would gather as much evidence that point to them, bill them, and if you go to court you have your evidence.

The tenant isn't stupid and knows he owes the rent, so he will probably pack up and leave before the court hearing.

It seems that you have a reason to evict them but its likely that you won't be able to get a court hearing until a few weeks out so sometime in mid Dec.  

As of today however due to a signed affidavit we will be given a court date to follow through with eviction and perform said strategy above with section 8.  

Use customized leases with state-specific templates and consult a lawyer for complex issues.