Here are some tips for renters looking to find the right place.
1) Always remember that there are lots of rental units on the market. This is a renter's/buyer's market. If something does not smell right, walk away.
2) Consider using a real estate agent. In the downturn, many real estate agents have gotten into the game of showing apartments. It costs nothing from the renter's pocket to use an agent. Agents have access to MLS listings and can pre-arrange appointments to walk a potential renter through a number of units on the same day.
3) Tenants should be familiar with the Chicago Residential Landlord Tenant Ordinance and their rights under it vis a vis security deposits, prohibited lease provisions, and other required disclosures. It is actually better to find a landlord who complies rather than either 1) a landlord ignorant of the law or 2) a landlord who does not comply with the law.
4) Check the cook county clerk of the circuit court website to see if your potential landlord is a party to any lawsuits, especially foreclosures. You can also check the recorder of deeds website to see if there are any lis pendens recorded against the property. Building code violations can also be a good clue that the landlord has a big problem. Landlords involved in foreclosures are usually not going to be good landlords nor will a tenant's tenancy likely extend the full term.
5) If the landlord agrees that anything is to be done before a tenant moves in, the tenant should not move in before the work is done. This should be a provision in the lease excusing the tenant from performance until the landlord completes any necessary work. For instance, if a landlord is supposed to paint a bedroom but does not, a tenant can safely assume that most likely this is 1) probably the landlord's normal practice and 2) the yob will probably never get done. Tenants should negotiate a small hold fee or security deposit until any of those sorts of things are completed. A landlord who waits on those sorts of things is likely waiting for the tenant's deposit to have the money to do whatever work needs to be done or does not really intend to do the work.
6) Tenants should not spend their own money on a rental unit until they are sure that they will be staying/leasing. I was contacted a few months ago by a lady who told me that she had terrible allergies. After doing massive remodeling in the property, she told me she discovered mold in the unit and it was hazardous for her to live there. The landlord had committed numerous CRLTO violations that would give her a right to terminate the lease. The tenant declined to move because she "spent so much money fixing the place up". True story. Don't do this.
7) Plan in advance. A tenant should look in plenty of time before needing to move. Tenants should not get caught in a situation where they must move and then might have to accept a less than optimal situation.
8) Tenants should inspect a rental unit THOROUGHLY. Check under the kitchen sink or in places where water flows for mold. See how drafty the windows are. Listen for traffic/train noise. Make sure everything works (turn on anything that might leak and let it run for a while to be sure). Make sure there are no stains in the carpet being hidden. Look "UP" - at the ceilings for signs of water damage or repairs to water damage. Document the condition of the place. Take pictures. Sign something that indicates any bad conditions that exist at the start of the tenancy so there is not question as to who is on the hook at the end of the tenancy.
9) Prospective tenants should talk to other tenants in the building to get a sense of the landlord's responsiveness and practices. If things are bad, other tenants will usually say so.
10) Tenants should go with their gut and should not act stupid. Trust instincts when they say "run". Do NOT trust a landlord that does not have paperwork or copies available - if you don't get your lease and receipt up front, you might never get it.
I could probably go on and on, but those should give tenant's a good head start on having a successful run as a tenant.