The Worst Deal Chicago Ever Made
West Loop lost a lot of free parking this summer, which has us talking about the city’s infamous parking meter deal. In 2008, City Council voted to privatize Chicago’s parking meters for 75 years in return for $1 billion. But in the years since, analysis after analysis has shown the meters were worth much more, and the city lost out on revenues while investors earn a profit as Chicagoans pay some of the highest parking rates in the country. While he was at the Reader, Block Club Chicago reporter and editor Mick Dumke investigated the deal after it first passed. He tells host Jacoby Cochran why Chicago went for it, who challenged it, and how we feel the effects today.
Some good news: Chappell Roan’s local weightlifters at Lollapalooza
If you enjoyed today's interview with Ravinia Festival's Artistic Director, Erik Soderstrom, learn more here.
Want some more City Cast Chicago news? Then make sure to sign up for our Hey Chicago newsletter.
Follow us @citycastchicago
You can also text us or leave a voicemail at: 773 780-0246
Learn more about the sponsors of this Aug. 5 episode:
Become a member of City Cast Chicago.
Interested in advertising with City Cast? Find more info HERE
Subscribe To Our Newsletter

Stay connected to City Cast Chicago and get ready to join the local conversation.
Latest Episodes
Why Massage Parlors Are Getting Raided in the 12th Ward
Two illicit massage parlors on Archer Avenue were raided within weeks of each other — including one next door to 12th Ward Ald. Julia Ram...

Who Will Replace Retiring Police Chief? Plus, Chicago's New Gayborhood?
The Chicago Police Department will be without a permanent police superintendent starting July 15, as current superintendent Larry Snellin...

'Your City Could Be Better': The Ultimate USA Trivia Battle. How Much Do You Know? — Presented By City Cast Chicago
See if your Chicago knowledge serves you well! In the first-ever Your City Could Be Better trivia episode, City Cast CEO David Plotz goes...

What Is a Tenant Bill of Rights? Plus, Cold Treats For the Heat
This week, Mayor Brandon Johnson pitched the Protecting Renter’s Ordinance, which the city calls a “comprehensive modernization” of Chica...

Your Guide to July 2026 in Chicago
As summer really takes off, the food fests, fireworks shows, and WNBA All Star Weekend have us really excited for July. Here’s your guide...

Extreme Heat, Indiana Fireworks, and 'The Bear' Finale
Extreme heat warnings, corn sweat, and potential thunderstorms could make this the most volatile weather week of the summer so far. Execu...

Seriously, More Parking Meter Drama? Plus, More Mayoral Candidates
Chicago’s infamous parking meters are up for sale. In a City Council committee meeting last week, alders got more insight into the mayor’...

How Quantum Is Already Changing the South Side. Plus, Heat Wave Approaching
Earlier this month, Advocate Health Care broke ground on a new hospital at the south end of the forthcoming 440-acre Quantum Shore Campus...

FCC Comes For ABC Chicago, The Bear is Back, and Get Free Coffee
The Federal Communications Commission has ABC 7 Chicago and other local stations in its crosshairs as the FCC has ordered an accelerated...

How Much To Run For Mayor? Plus, Elise Malary Plaza and City Hall Art Missing
Secretary of State Alexi Giannoulias, who has been floated as a potential candidate for mayor, recently received $255,000 from a local un...

