Security deposit return or keep? Help!

[Jessica Perez]

Back story: Rented to a couple with a young daughter, contract was for 6 months, ending November 1st 2021. Girlfriend called police and filed a restraining order against boyfriend. He moved out beginning of June. I agreed to allow her to stay on, she promised me she could handle the rent. Turns out she couldn't. She moved out yesterday and called me to give me the keys. Boyfriend called today wanting to know when he's getting his security deposit back and told me he wouldn't give back the garage door opener until the money is in his account. The apartment is really dirty, tons of nail holes, a broken ceiling fan, and ants everywhere. My question is: do I write up all the repairs that the apartment needs and subtract from the security deposit or do I have a right to use the security deposit to cover losses from the breach of contract? The Girlfriend wants nothing to do with the deposit. She asked me to handle it with him. She just wants to be done with the situation. He's a hot-head and behaves ignorant so I want to make sure I have a very clear explanation within the law for Illinois. Thanks for all the help and insight in advance!