Now the CHA folks themselves (in the office)  will make you jump through hoops for initial and ongoing inspections.

You then need to ensure the property will pass the CHA inspection.

@Billy Cha Thank you for your helpful input, will check them out!

You can contact Chicago Housing Authority (CHA) assuming that is who the section 8 voucher is for and request a rent increase.We recently did this with one of our properties and were able to raise the rent from $956 to $1249. 

Instead of raising rent and scaring them away (their leases are both month to month right now) I was hoping to work with CHA to get them qualified for the voucher program but I need to register my property first.I believe I also need to register as a vendor with the City of Chicago first and I am curious if anyone has advice on that process or how long it takes as well. 

Turns out she used to oversee Rehabs for an out of state investor. cha-ching!

Do you do section 8 through CHA and was it difficult to get your properties certified for Section 8?

So yes, I'm sure I want to find great tenants where their rent is 80% (if not more) paid by CHA (Chicago Housing Authority).

That said, it's best to give 60 days notice to CHA (Section 8) tenants. 

Tenant screening is always important, and learning the ropes with CHA is necessary.