I live in Chicago, what is the best time to buy a car as far as supply and demand?
To be honest, your location doesn’t really have much to do with it. Especially with a major city like Chicago, the best time in terms of supply/demand and in turn, pricing, is almost always the end of the model year. The Consumer Reports link at: http://www.consumerreports.org/cro/cars/new-cars/buying-advice/best-time-to-buy-a-car-1204/overview/ does a solid job of detailing some of the ins and outs of timing. They are a good non-biased consumer advocacy group. The end of the model year is what you really want to push for in terms of getting the best deal supply/demand wise. They are pushing the old models out to make room for the new ones and you can get deals you never can at other times of the year. The next best option listed on the Consume Reports link is probably the end of the calendar year idea (December). Hope this helps and best of luck! Sources: <