I've been to Chicago but never ridden a bike there, but driving I found a lot of the streets downtown to be pretty good, and more of them to be pretty bad. I spent 7 days in England but it was almost 20 years ago and neither drove nor rode a bike there, but the pavement conditions seemed to be similar to here, and yeah a lot more bricks. I wouldn't want to ride a bike on brick very much/often. In town here (Fort Wayne) we have a lot of roads with pretty smooth asphalt, a lot of roads with really old cracked and potholed asphalt, and a TON of buckled concrete around the suburbs. Back roads outside of town range from very good to very bad condition, generally asphalt. Heavy use by horse drawn carriages and construction traffic (semi trucks, dumptrucks, etc) on back roads of my commute beats up the roads and in turn the rider. Buckled concrete IMO the worst. The subdivision I live in pretty often represents the worst road conditions I encounter. Good thing it's only the first and last 1/4 mile of my commute.