The city comes alive.
I spent a few days in Chicago at the end of November. It's a huge city that's only a few hours from Madison, yet I don't get there very often for some reason. Probably because I've been focused on the natural world for the last few years.
For this Chicago visit, I didn't have any agenda. I stayed with Ali, whom I met through CouchSurfing in Madison last year, and spent a ton of time walking around Logan Square where he lives. It's kind of a trendy Hispanic neighborhood on the north side, and the weather was just warm enough to walk all day and not get cold. I also met with some other CS friends for a night of classic video games and drinking at the Emporium. I did pretty well at Galaga, sucked at PacMan, and was disappointed that they didn't have a Robotron machine.
Chicago is a neighborhood-oriented city, but the place I tended to meet people who lived on opposite ends of town was in The Loop. I spent far too much time walking around and watching others buy ridiculously overpriced crap. Then I went to the bar at the top of the Hancock Tower. Ali's friend Monina and I spent two hours watching the sun set and the city come to life.