Oh man. I may not know much about really fancy food, but after 3+ years of veganism, I
know vegan restaurants.
The Chicago Diner: Order the chocolate-chip-cookie-dough peanut butter milkshake, by far the most popular shake, or any other shake, but skip all the other desserts; Karyn's Cooked knocks them out of the water.
Best things on the menu: The Thunder Salad with any kind of garlic dressing, Thai Tofu, Scrambled Tofu Deluxe, Biscuits & Gravy Hash Scrambler
Worst things on the menu: BBQ Bacon Cheeseburger, Swedish Meatballs, BBQ Wings, Mac & Cheeze, Grills Gone Wild. It's usually safer to avoid the specials.
Alice & Friends: Creeeepy religious cult atmosphere and not very vegan-friendly at all. Lots of eggs and cheese on the menu. I got a tofu scramble and it was terrible.
Karyn's Cooked: My favorite vegan restaurant in the city. Don't mix up
Karyn's Cooked with Karyn's Raw, or you'll be one sad puppy. The burger with cheese is the only meat-like veggie burger I've ever liked. And I don't just like it, I love it. The only dishes I wouldn't recommend would be the falafel & hummus - there's better out there. You have to get a dessert; the slices are huge and moist, and the frosting is incredible. Get a scoop of vegan ice cream with it.
Veggie Bite is way out on the Southside, but is a fun visit; it's so full of junk food that it's basically a vegan McDonald's. Picture 'cheese' fries, Italian beef, etc., and you can take your meal and a milkshake out to the patio and chill out in the great weather.
Blind Faith isn't a bad restaurant, but it's pretty much what omnivores picture vegetarianism to be: decent but overall bland. The atmosphere can be very crunchy-granola - and in such a pretentious way, too. The booths are usually full of aging hippies and their very pale children. Skip the desserts - I once ordered the Sesame Stick which I couldn't break with my teeth or hands. Made it pretty difficult to eat, as you might imagine.
South Vegetarian East is in kind of a sketchy area, which is why I hesitate to recommend it to tourists - I really wouldn't recommend taking public transit there - but there's no denying the food is great. It's unapologetically bad-for-you soul food. And I do mean that literally: it's been shut down due to health code violations at least twice (mice, etc.) so go at your own risk.