Greg, of BOTW.org (Best of the Web), talks about how people overlook the value of regional and local directory listing. He is surprised at the lack of submissions to the regional section of their directory.

If you own a Chicago real estate company does it really makes sense to be listed in a directory under /real estate/ with dozens to hundreds of other websites. Or would you get much greater value (and some traffic) to be listed under /Chicago/Real Estate/. Getting listed in directories under the city name not only provides greater value for rankings it also provides real quality traffic. Will you get a ton of traffic from regional directory listings? I doubt it. At the same time the traffic you do get will be pre-qualified. It is not about the “amount” of traffic you get. It is about the quality and conversion of that traffic.

For your rankings it is better to have your site associated with other Chicago real estate companies. This clearly tells the search engines you are “truly” about Chicago real estate. Remember search engines judge your site by the company you keep.