Chris travels to Chicago a lot for work at the Merchandise Mart, Most of his choices are meat focused...but he likes
"Howl at the Moon" (duelling pianos) for entertainment and food
http://www.howlatthemoon.com/locations/location-chicago,
"Harry Caray's" as well for steak (sorry) and seafood
http://www.harrycarays.com/ and
the "Kinzie's Chophouse" again for steak and seafood
http://kinziechophouse.com/. ,
he thinks the burgers at "The Bull and the Bear" are great
http://www.bullbearbar.com/. I took a peek at their menu and it looked interesting and had some veggie choices.
A vote for pizza at Lou Malnati's from both him and our boys
http://www.loumalnatis.com/....I'm not a fan of deep dish but it was a good tourist stop.
Hiigh Tea at the pennisula hotel is something I'd like to do next time I get to chicago, hopefully with Becky since we didn't get to do it last time, but the cafe at the base of the hotel serves an excellent pot of tea (in Denby no less) and wide array of pastries that were yummy.