As a resident of the EV and a moderate foodie here are a few of my suggestions.
Prune-if you can get the steak for 2 which isn't always available grab it and never look back.
The Spotted Pig-just go and order anything
The Blind Pig- Pub style, good burger and nachos
Via Della Pace-awesome risotto and a brunch that while it isn't cheap because of booze you'll leave full and drunk.
Esperanto-cheap very tasty brunch with a comp drink. Their drinks are strong. The dinner food is very good and based on Latin American cooking.
The Sun Burnt Cow-Unlimited drinks Aussie style brunch.
Zum Schneider-Took my Germany born father there for German food for the first time in 25 years and he loved it. Also great beer.
Freemans-I like the downtown location not the lunch thing in the Chelsea Market.
Max's-Great Italian and cheap
Barbone-Great fancy Italian and moderate pricing.
Black Iron burgers- open late for drunk munchies. Also a bar and has malteds.
Crif Dog- this seems to be a real thing for you Chicagoans, you like your Vienna sausage dogs.