HELP! Buying a Chicago Property with Defaulted Tenant

[Connor O'Brien]

Hi All, 

I am currently in the attorney review period buying a 2-flat in Chicago. My attorney demanded the bottom unit be vacant by closing as seller had given 30 day notice to a month to month tenant when it was put on the market. The seller's attorney letter stated the following: 

There was no security deposit 

Tenant ceased paying a few months ago 

They cannot find the lease but " (it) expired long ago and the tenants are month to month." 

"The first floor tenant has been properly served with a 30-day notice to quit the premises, and the time has elapsed. An eviction has not yet been filed" 

I plan to: 

Ensure there was never a security deposit. If there truly never was one I want to offer the tenant cash for keys. 

Is there a legal document I need to have the tenant sign when they leave the premise? If so can I deal with the tenant directly before closing? 

Also, the second floor lease was also "lost" and expired. Can I provide this tenant with a new lease before closing? They currently use CHAC. Do I need an inspection or anything else to continue receiving the voucher? 

Thanks for the help!

-Connor