If you like jazz, you should try to hit the Green Mill on Wednesday 12/14. The place has a great atmosphere and Kurt Elling will be there. There are a few good places to see live music within close proximity of the intersection of North Ave., Damen and Milwaukee. Liquid Soul plays at The Note on Milwaukee every Wednesday. If you'd like a quaint restaurant with good food and very friendly service, you should check out Club Lago at 331 W. Superior St., ask for Giancarlo or Guido and they can give you some direction as well. Enjoy!
Check out:
http://www.subt.net/
http://www.thenotechicago.com/
http://greenmilljazz.com/index.html