Via chicityclerk.com

Residents living in residential parking zones no longer have to visit the City Clerk's Office or the Alderman's office to get residential parking permit guest passes. 

Online purchases are processed at City Clerk del Valle's office in 2 to 3 business days.  Depending on mail delivery, you should receive them shortly thereafter. There is no service fee. The cost for one book (15 passes) of guest passes is $5. 

Residents can purchase up to two books every 30 days as set by ordinance. To purchase residential parking permit guest passes online, you must have purchased a current 2008-2009 parking permit from the City Clerk's office.