UPDATE 10/28

The City of Chicago has retained security consultant Neil Sullivan to aid with the Obama rally planning at a rate of $100-an-hour with a $60,000 cap, the Sun-Times reports.

Sullivan had been hired to coordinate security for potential World Series appearances by the Cubs and White Sox and "turned his full-attention to Election Night" once both teams were eliminated from contention, the paper reports.

UPDATE 10/27

The Chicago Park District had yet to receive a permit application as of Monday...