Have you guys thought about using Zipments.com to make some extra money? I'm an intern for Zipments and I thought integrating with the bike community in Chicago might be mutually beneficial.

Basically, companies/individuals post delivery jobs to Zipments.com and let local couriers bid on them. That's not to say "who will work for the lowest wage?" because couriers can also be selected (or not) based on their past performance and experience. It seems like it could be useful, especially if you can make deliveries on your daily route. Also, if you want to  get live updates of job postings, you can follow the Zipments Twitter feed by texting 'Follow ZipJobsCHI' to 40404.