Dick's is always good for entertainment and people.
I used to go to the Hilton overthere quite a bit on meetings, and less than a block away there was an Irish bar that I parked myself in for a number of nights. I don't recall the name, but it was out the front door of the hotel, go right and 1 block. cross the street, down 2 doors and there it was. Getting home for some reason was more complicated some nights
Haven't been to Chicago in 3 years now - but it's still as cold and windy as ever. They just got blasted with another round of snow, so bring your woolies!