Chicago Parking Meters Will Be US's Most Expensive Chicago soon will have the nation's most expensive downtown parking meters. On New Year's Day, meters in the city's downtown Loop area will begin charging $6.50 an hour - up from $5.75. A report from the San Francisco Municipal Transportation Agency says the rate change will make Chicago the city with the most expensive metered parking. The company that operates the meters plans to have all machines set to new rates by the end of February. Former Mayor Richard Daley got the City Council to approve the company's 75-year contract in 2008. In return, the city got a $1.1 billion payment - much of which has already been spent. Current Mayor Rahm Emanuel has ordered an independent audit of the deal, which is now largely viewed as a financial disaster.