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The Sun-Times and the Trib have various details on the city's new parking deal. In short: the city sold all the parking meters to Chicago Parking Meter LLC, aka two Morgan Stanley funds and a parking company, which will subsequently jack up the rates, most from $0.25 to $1. The immediate reaction to any price increase is outrage, but in the abstract it's clever:
Problem: The city is broke and needs more money from parking meters (among other things).
Solution: Sell the meters, take the windfall from the price increase up front, and split the PR burden with a private company (City Council apparently has final say over rates, so they're not totally off the hook). If people are willing to pay, then, well, they're willing to pay; if not, the city's already cashed in.
It's also worth considering the substantial increase as a punitive tax on driving in the city--which will surely piss people off, of course, but it could also reduce congestion and divert more people to the CTA or other forms of transportation like biking or walking. Or Segways, which are of course hilarious. Higher rates could also lead to more parking violations, and if I read things correctly tickets would still get paid to the city, diverting what amount to parking "fees" back to the city.
Full disclosure: I don't own a car and rarely drive, and when I do it's often during free meter hours (I have no idea, but offhand I'd say I've spent less than $100 on parking meters in 7+ years in the city), so I'm obviously going to be more inclined to look on the sunny side than a lot of people. But of all the cynical moves that have arisen during the city's long dark night of the budget, this one at least has some upside.