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Chicago Used Cadillac Escalade Cars. Use Yahoo! Autos to find Cadillac Escalade used cars in Chicago or other nearby cities. You can refine your search for Chicago Cadillac Escalade used cars by make, model, year, price, mileage, or distance from your zip code. Every Chicago used Cadillac Escalade listing is noted whether it is a private seller or dealer, and many of the Cadillac Escalade listings come with several pictures.