Although CheapCarsChicago.com may not appear to be domain of much value to many here, I think it is quite a good name to start your 'Domain Adventures' with.
Why?
Because it is easy to market to select end users.
Simply build a database of used car traders in Chicago, and contact them.
Could even be worth the cost of a small lineage ad in Chicago Used Car Classifieds.
Good Luck
DOMiNIC