Late last night (like from 1 to 4, I don't know why) and this afternoon I hacked together a merging of Google Maps and Chicago Reader rental classifieds. I give you the result (it takes a while to load).
I like Housingmaps.com a lot, but Chicago Reader (so I've been told) is one of the best ways to find a place to live in Chicago. Craigslist is so-so. Compare the results on the two maps and you'll see that it's true.
Step one: Perform a search and copy-and-paste the resulting URL into my code. You're looking at 1 bedrooms in 60613, 60614 and 60657, priced between $600 and $1000.
There are two ways to find the location of a property. If the classified ad has a map link, I don't need to find the address. I can follow the link; it redirects me to a new URL that has the GPS coordinates in the query string.
Method two involves me parsing: "Street1 and Street2" or "#### (Direction) StreetName". It's not perfect, but it's pretty good. I can then ask Google to attempt find the coordinates from the address I harvested. In total, I can find the coordinates of about 80% of the ads.
If anyone's interested in the source (C#), drop me a line.
Kudos to Google Maps on such an excellent and interoperable product.