I'll take the vegan dining question, but only for places I've tried. In no particular order:
Chicago Diner-Very good, in general. 100% vegetarian menu, many (mostly?) vegan. Their menu frequently changes, so check out their website. And try a shake!
http://www.veggiediner.com/wp/ Pick Me Up Cafe-Diner style. I believe they still do vegan French toast, which is awesome. Some other vegan options (marked on the menu, but be safe and ask). They use the same deep fryer for everything (they have calamari on the appetizer menu), so keep that in mind if ordering anything fried. No website, unfortunately.
Handlebar Cafe-Lots of tasty vegan sandwiches and breakfast items. Lots of different different beer as well, if that's of any interest to you.
http://handlebarchicago.com/ Loving Hut-Formerly Alice and Friends. 100% vegan Asian. Haven't eaten there since the change in names, but I've heard it's almost entirely the same. Very good. I've heard John Joseph from the Cro-Mags eats there every time he's in town. I don't know if that's true, but I want it to be, so I'm sticking with that story,
http://lovinghut.us/chicago/Bleeding Heart Bakery-Delicious baked goods. Many vegan options. Staff is knowledgeable, and sometimes even friendly.
http://www.thebleedingheartbakery.com/That's all I can think of at the moment. I will add more if anything comes to me, The only places I've heard that should be avoided (but have not tried) are Veggie Bite, a vegan fast food place that many say is bland and not very good, and Soul Vegetarian East, a vegan soul food place that occasionally runs into disgusting problems with the health department.