I am not seeing the same risks that some of you are suggesting if I get a full year of rent ahead of time. I could put in a clause that states if they wish to renew for another year the rent must be fully paid again for at least 6 months in advance.
Illinois is very tenant friendly state and Chicago takes it to a whole new level but if you stay on top of rules I don't think it should be that much of an issue.
Is Notice Required if a Lease Expires?
A written lease expires automatically when the lease says it does, usually after one year. However, if the Chicago Residential Landlord and Tenant Ordinance (RLTO) applies to your rental unit, you must give the tenant notice, in writing, 30 days before the end of the lease, that you will not renew the lease. If you do not, the tenant can stay an additional 60 days past the expiration of the lease. After 60 days, you can file an eviction lawsuit, without giving a 5, 10, or 30-day notice.
Rent Payments After Expired Lease
If you accept rent after the end of the lease, you will create a new month-to-month lease with your tenant. This new tenancy will have the same rules and terms as the lease you were using. If you want to end the lease at some point in the future, you will have to give a 30-Day Notice as described above.