By the way, just to illustrate this with an example so I don't sound like а windbag.
Great that you mentioned Chicago.Directory because its a registered domain with virtually no content on it. A search for "Chicago Directory" does not bring this site in the first 10 pages.
But yeah, its easy to judge an empty domain. Took my time and found a developed one - Dallas.Directory. Google search for "Dallas directory"? Nothing in the first 10 pages. As a matter of fact in both searches I did not found a single .Directory domain. So there you have it...