You and your friend could also call 311. This is a the information number for Chicago. Another good recycling resource is the resource center http://www.resourcecenterchicago.org/. The drop off City's drop off centers will only take home waste. For a painter I imagine the line that you are repainting your house will only work the first couple of times.

The City of Chicago runs the Household Chemicals & Computer Recycling Facility at 1150 N. North Branch (Goose Island near Division & Halsted) which accepts some hazardous materials such as oil-based paints, thinners, areosal paints, solvents, etc, etc.

Personally, I think retailers should help collect used paint--if they can help sell it, they should help clean it up by offering to collect & properly dispose of it. I've seen paint lining street drains where people have poured it down the sewer...nice...  

FYI--Green Maker sells American Pride which is no VOC, I think.

Here's the city's link & there's also a link for a paint exchange - http://egov.cityofchicago.org/city/webportal/portalDeptCa ...

To get rid of those paint buckets, brushes, paint, or anything and I do mean ANY usable thing that you no longer want, go to http://www.freecycle.org and click on the link to your city. there are freecycle groups all over the country now that connects people who have excess stuff with the people who can use it.  Don't landfill it! Freecycle it!