the only soft serve i know of in the chicago area is at soul vegetarian and at veggie bite. i've never seen any at chicago diner or pick me up or any of the other vegan friendly restaurants in the city.
if you go to chicago diner, i recommend the fajitas and the reuben. i also recommend the raw cheesecake (better than ANY traditional baked vegan cheesecake i've had, ever). if you get a milkshake, go for the chocolate chip cookie dough with peanut butter. its gluttonous, but delicious. oh, unless they have the pumpkin (seasonal). if they have pumpkin ice cream, get something with that. mmmmmmmm! also, they have some VERY good brunch options, if you don't go there for dinner. their savory brunch dishes are best, i don't recommend pancakes or french toast there
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At the Chicago Diner, I totally second the reuben and the chocolate chip cookie dough with peanut butter milkshake. I've also had a great raw vegan lasagna there. Normally I am not into seitan, but I really really (omg) enjoyed the reuben.
there's this russian tea place near the center of town that has a really awesome simple vegetable stew. (you know, cause you might become overwhelmed with all the fake meats you've eaten at the other places and whatnot, and need a real simple veg-based dish) the place isn't vegan, but the stew is.
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I AM SO JEALOUS ... of the vegan soft-serve you will eat alone!!
actually I took a trip to chicago last year and did a zine on it with lots of restaurant reviews:
http://people.umass.edu/lleake/18longdays.html -- wanna free copy?
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