I recently went to PyCon 2008 in Chicago. I would recommend this conference. I am currently learning python and I found that at this conference there was a track of tutorials and talks aimed at the python beginner. I meet a lot of people and I had a pretty good time.
It is going to be in Chicago next year as well. If you are a developer and you live in Chicago, why not go and check out the conference while it is here in Chicago? It is not very expensive and it is a lot of fun.