At the last WIA meeting we discussed a "sketchcrawl".
It's all started with the John & Bill Show which will be at the Portage Theatre (the show's website has directions).
The John & Bill show's tickets are now up for sale. We're planning on going for the Saturday Matinee (at 1:00 pm), which costs $15 to get in. http://www.thejohnandbillshow.com/tix.html
As for the sketchcrawl, we're planning on taking public transport around town, so if you don't have a pass, I would suggest getting a 1-day cta pass. This allows for unlimited rides on el trains and buses and no worries about change. The 1-day CTA passes (aka. FUN pass) are available at Customer Service areas of Jewel or Domincks for $5.
So the plan is to see the Matinee with John Kricfalusi (of Ren & Stimpy) and then go around to various places to sketch. This is based on the "Sketchcrawl" as created by Enrico Casarosa. To get the idea check out his sketchcrawl blog: http://www.sketchcrawl.com/blog/