A management-consulting firm by the name of Runzheimer International released a report that revealed Detroit, MI as the most expensive city U.S. city in which to own and operate a motor vehicle. The firm calculated it costs $11,844 per year to own a mid-size car like the Ford Five Hundred in Detroit, with nearly $5,200 of that total going towards insurance alone.
The article from CNN/Money has a list of other cities and their cost of car ownership, which reveals that Philadelphia comes in a not-so-close second with an annual car ownership cost of $10,672.

This is one report I can attest to personally, as last year I moved from Detroit back to my hometown in Ohio where comprehensive coverage for my 1994 Mazda Protege was less expensive than the cheapest liability coverage I could find in Detroit.

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