We are in the process of reaching out to the local Chicago technical community to find out if there might be couch surfing opportunities. So far, Brian Moloney has agreed to send a note out to the Chicago Djangonauts.
For our part, we'll extend a couch or two (maybe with a personally-guided microbrew tour) when DjangoCon returns to Portland next year - with preference to our friends in the Chicago community.
Those offering Chicago "couch shares" will be encouraged to post on the Room Sharing Wiki.