Chicago tenant eviction questions

[Patrick Moore]

First off, let me begin by saying evictions in cook county are the worst... 

This is my first rental. It's a 3 flat on the southside of Chicago and I live in one of the units(House hacking it).  

I filed the eviction, completed everything, and the judge granted us possession. 

Then the tenant came up with some sob story and managed to schedule another court date. He fed the judge another sob story and managed to get a 4 week extension. It's been 7 weeks since we got the order of possession and he received his extension.  

He started moving his belongings out eventually, slowly. Now I haven't seen him at the property in over 10 days. There is not much left in the unit but there is some things like a fish tank, mattress, and loads of garbage. I sent the tenant a text about 10 days ago asking if he was done moving his belongings out. Surprise, he hasn't responded. 

At what point is it legal for me to change the locks and start cleaning the place up so I can start to recoup my losses. I haven't received rent from the unit since July! I can't wait to get this property back into the cash flowing side of things.   

Do I have to wait for the Sheriff to come before I can change the locks and remove the rest of his belongings? Can I just move his crap to the front/backyard and tell him he's got 24 hours to collect his belongings and then pitch it all. 

[Mark Ainley]

@Patrick Moore Your options can fall into a grey area here.  If you want to be by the book, you will wait for sheriff.  If you want to be aggressive, find a way to trick the tenant into saying he has vacated.  Text him something like "water is coming from under your door...if you still live there please let me know and handle it otherwise let me know so I can go in and address the issue."  That was an off the top of my head thought but can probably be more creative.  Or go in and move his stuff to the garage or basement area just in case he comes back around.  Or just go in and toss it which is the most aggressive and below board option but most of the time results in a non-issue.  Worse case the guy comes back and you give him $1000 to make the issue go away.