Legal Question in Landlord & Tenant Law in Illinois

Depends on the locality and the kind of property. For example, Chicago has a landlord-tenant ordinance that prohibits prepayment requirements in covered rental units. In places where there is no other local restriction, however, a landlord and tenant can pretty much contract as they wish - and could agree that the tenant will deposit properly dated rent checks. But as a tenant attorney I wouldn't advise doing so unless you have no credit and are sure the rental unit will be habitable the entire term of the lease and/or enter into some kind of separate agreement concerning the terms and conditions of when the landlord may and may not deposit your checks. That being said, if the landlord has a mortgage on the rental the mortgage also may prohibit the landlord taking rent in advance -- and this may be the landlord's way of trying to 'skirt' that requirement. I have not seen this kind of requirement in many years, and the only time I did was when the tenant was in default already and this way a way of 'guarantying' future rent payments.