Originally Posted by cliff_rock

You might want to try the Chicago Reader. It is a free local paper that's pretty widely distributed and heavy on the classifieds. It was probably THE source for this sort of thing pre-Craig's List.

Originally Posted by biggestbopper

I talked to some folks I know who are in the rental business in Chicago. They only advertise in the Trib. Because, according to them, their experience is that ads elsewhere bring in very low class folks.

By the way, traditionally, in Chicago, especially in the "real" neighborhoods, the only advertising done is to post a little sticker on the front door of the building.