Consistently Late Rent Chicago

[Michael Wnek]

I was wondering how people have dealt with tenants who chronically pay rent late. Our current situation is a House hack in Chicago were we have two tenants. We took over the property in May and decided to let the current tenants stay, renewed with new leases during the summer which included raised rents. Prior to the new leases we received rent on time. After the rent raise we have yet to see payment on the first of the month. 

I know that Chicago allows for a 5 day grace period before any fines can be handed out or eviction can be started and so far we have always received payment before the grace period ends. 

We plan on not renewing the leases so we can complete rehab work but thats not until next year. In the interim i am curious how other Chicago land lords have handled situations like this.