The Chicago Drupal community has a long and proud history as one of the most active and vibrant in all of North America. The mission of the Drupal Chicago is to create an open community among everyone interested in the Drupal open source content management platform.
The Drupal Chicago Meetup Group (http://www.meetup.com/drupalchicago/) holds meetups and hopefully provide something of interest to everyone. Presentations and speakers are aimed at a general audience, with site show-and-tells, module demonstrations, news and announcements, and question and answer sessions. If you are new to Drupal, this is a great place to start and continue to learn about new Drupal things.
Volunteers in the Chicago Drupal Group also organize MidCamp - Midwest Drupal Camp (http://www.midcamp.org/). Drupal camps are multi-day events that can include training days, session days, code and documentation sprints, and social events. Held annually in March, MidCamp is quickly becoming one of the larger and prestigious Drupal camps due to its high level of speakers, content, accessibility, and attention to detail.