Each year around Christmas time, the Chicago Tribune puts together a benefit concert called the "Songs of Good Cheer". It's basically a big, happy-feeling Christmas Carol sing along with the audience. It's the kind of thing that will give you some happiness in the cold, dark winter.
It falls into several of my goals:
#74 : See 10 shows, musical. play, or other
#35 : See 6 concerts a year
#21 : Spend at least 1 day a month in the city