Basic Python - a subset of the core language elements. Cover the import command, but don't cover any modules. scope, lists vs tuple... that stuff, but don't cover lambda and other things that would make someones head explode.
Python for Java programmers - It's similar, but different.
Python for (other language you know) - If you have experienced the transition, share it with others to make it easier for them.
Under the hood of Python - or what ever you want to call the interaction between = and __eq__() and all the other things listed here: http://docs.python.org/ref/customization.html
Python's Dark Magic - the pros and cons of messing with __magic__()
Intro to easy_install and PyPI.
There are lots of programmers in Chicago that don't know Python, so many of them won't bother going to a python conference. Some will come anyway and walk away still not knowing python. I don't expect anyone to make them an expert, but I think a quick run through of the basics can do a lot.