So this Friday I was planning on being by myself on an over night layover at O'Hare. My friend elected to join me today. He has never been to Chicago, but has always wanted to visit. We can get downtown by around 9:30PM. I know that's kind of a late start, but I set this trip up with no plans on heading downtown. I've been in the city itself around 6 times, and the one weekend night I spent in the loop was kind of underwhelming.

Anyway all of this being said if you had to try and show someone as much of Chicago as one possibly could on a Friday night. Hitting some bars is certainly very much on the menu. What would you do?