Yeah, if you can pick a neighborhood to start from that will help. There are many, many choices. That being said:
Ginger Man: Hanging out in the back "lounge" room at GM and sipping on some great beer and tasty food may be one of my favorite things in life.
Blind Tiger: Great beer list, friendly people, awesome place to hang out.
McSorely's Old Ale House: About as local as you'll get. They have 2 beers, light or dark, and they come 2 at a time. Walking into this place is like stepping back in time, you need to go here just to see what things used to be like.