A car's value easily depreciates and logically it's much more practical to get a used car over a brand new car if you're on a specific budget. There are many great finds in authorized used car dealers with the help of carfax you can have the proper guide in getting your next "new" used car.
In Chicago, lifestyle can be more upscale but that doesn't mean getting used cars in Chicago is not a common thing. UsedCarsChicago101.com has a good inventory listing of newer model cars, van and SUVs. Prices depend on the year model but nonetheless competitive with other dealers. Let's say you like Honda Odyssey then you've got the right place for your purchase.
Check out UsedCarsChicago.com's featured blog post @ http://www.usedcarschicago101.com/blog/ for a more interesting read about used cars, recession and their site.
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I have to agree with you, Ayie. When my former van ( I had just paid it off ) was totaled when a tree fell on it two years ago in a winter storm, I found a used van at the dealer. It had 10,000 miles on it and had been a rental van for one of the major car rental agencies. It was a Dodge Grand Caravan with all sorts of bells and whistles and much more reasonably priced than I had anticipated.