Chicago law requires landlords to allow tenants to sublease their apartments if requested. Here's what else you need to know about subleasing in Chicago.This group helps to find rooms, roommates and apartments in Chicago, Illinois, USA. Search short term and month to month rentals. We created this community to make the process of finding a new home, tenant, or roommate, just that bit easier. In Chicago, landlords must approve reasonable sublease requests unless the property is owneroccupied with six or fewer units. Facebook marketplace will be your best bet. Then Craigslist will be the next best.