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.