Despite the common complaints, I'd say Chicago is pretty good. Our mayor is a big bike rider and bike advocate. In the last few years there have been a lot of bike lanes created in the city. Regular drivers are very tolerant as bikes riders plentiful and growing. No one has yelled at me or buzzed me.

On the downside, cab drivers are generally jerks. They are bad enough when you have to share the road when driving a car. When you're on a bike the whole "major injury/fatality" quotient goes up a lot. Clueless folks driving in the city while talking on the cell phone is pretty common too. They normally aren't being mean, just stupid. Of course their attitude towards us probably doesn't really make getting hit any less painful. Oh yeah, and that whole winter thing w/ blizzard like winds.