Gave tenant 4 month notice may not leave, what to do?

[Mario Morales]

Hi again everyone. I text my tenant today to check that we are all good for his moving out date, April 1st. He text back that he wants to "talk to me in person". He is on a month to month tenancy and I gave him the 4 month notice required by chicago law. I feel like he is going to ask for more time, which, if I take the same amount of rent, I will be in a month to month tenancy and will require another 4 month notice. I believe, that if he stays by law, it's double the rent since he is staying past his lease. I don't trust him to leave, he always pays on time but, his rent is under market by $500 and he destroyed a white oak tree I planted, I have him on video, he doesn't know I have the video. I can't have him stay because he is paying way under, he is not a good tenant, and I need to renovate the apartment to get market rate. 

What to do?