Parking

Chicago, IL - Parking on most streets in Chicago will cost you at least $2 an hour. In some busier areas that jumps up to $4.50, and the downtown Loop area can run as high as $7. You’d be hard pressed to find pricier street parking in the United States. A 2019 study by the parking services company Parkopedia found only Miami Beach and New York City are more expensive.  But this wasn’t always in the case. Before 2008, parking in the Windy City was a relatively reasonable 50 cents per hour, no matter where in town you were. But 14 years ago the City Council, at the urging of then-Mayor Richard M. Daley, sold the entirety of the city’s street parking system to a private company for a cool $1.15 billion.