I'd reccommend using the metromix website, they're usually up on things in terms of bars as well as what's going on in the city.
http://metromix.chicagotribune.com/
If you're looking for live jazz music, The Green Mill is one of the oldest places in the city. It's one of my favorite places.
For shopping, Lakeview has some fun shops on Halsted, Clark, and Belmont.