I was there in May and stayed at the Holiday Inn Express which I think is a little south of Lincoln Park. There was this badass restaurant nearby that had pizza, ribs, burgers, beer, salad, some awesome lemonade punch drink with fruit in it, desserts, mac n cheese, EVERYTHING. Kind of a small place, laid back atmosphere, nothing classy. Really friendly people. Large portions for cheap, but everything tasted great. Ronny's Steakhouse on Randolph Street, I highly recommend it.
Check out all the shit on Rush Street, there's a lot to do as far as stores and restaurants and whatnot. As far as the bars go, I can't remember where we went (I drank a lot) so I'm no help there, I just went wherever the rest of my group went. Ask some of the people there, they will point you in the right direction. Drinks are pretty expensive everywhere you'll go, I do remember that much. And a lot of the bars there were open til 5am which was pretty cool