Wow thank you guys so much. This is pretty much exactly what I am looking for. I spoke some more with my friend, and said he was more interested in seeing Chicago "at bar level". So with that in mind I took a look at all of your suggestions. And it looks like the area around the Map Room has quite a few spots, so I think we might head that way. Since we are about 24 hours out looking at the traffic info at least for tonight the CTA looks like it would be marginally faster. Although obviously tomorrow is a different day. Seems like there are a few bars around the map room that should provide enough to make it an evening.

Thanks again for all the excellent and detailed ideas. ^ Really made this easier I don't think I would have found some of these spots without your help.