Speaking on the availability of vegan food in Chicago, it can't really be that hard. I live in the suburbs and there is a vegan place called
Shree about 2 or 3 miles from my house. My room mates have tried it and said it was really good. They aren't vegans or anything. They are just open to trying most any kind of food.
The website has a few points of interest. Number one being the small swastikas across the top. The other being the "People's Verdict" section at the bottom on the page.
I'm definitely trying to augment my diet with more vegetables and what have you, so the idea of a 3 or 4 day per week vegan diet interests me.