Ok I have a conundrum. I'd like to start communting to school and work downtown. I recently moved about 10 miles from there, but I have one big obstacle. The neighborhood on the west side of chicago is, well, bad. I drive through it all the time to dodge traffic on the expressway. So I'm familiar with the terrain so to speak. For those from Chicago, the route I'm thinking is a straight shot down Madison Street. But once you cross Austin, it get's progressively worse until you get to about Western Ave (which is about 4 miles).

So, for those who commute in the city (doesn't have to be chicago) do you ever traverse bad areas? If so, have you had problems? I've seen people riding their bikes down Madison in the bad area, and I can tell they're a commuter. They're also riding very fast

For those who live in the Chicago area, do you know any route to get from Oak Park downtown? I thought about going a little bit north then cutting across, but I'd have to scope that out. I know that south isn't much better. Or am I being stupid about it? Am I really going to have an issue?

Thanks everyone!