As a cycle commuter I've lived in Chicago, Cleveland, Pittsburgh and Nashville. Would rate Chicago as the best and Pittsburgh as the worst. Chicago was flat and while not 'cycle friendly' at the time things were readily accessable from the saddle. Plenty of side strreets running parallel to main boulevards if one wanted to deal w/stop signs instead of traffic. According to some posts here on BF Chicago has embraced cycle commuting w/t addition of bike lanes and commuter routes. And R. Daily, Jr. is an avid cyclist, which helps alot.

Cleveland is similar to Chicago as far as terrain is concerned and being a lakefront city the weather is similar. The main streets, at least on the east side are pretty wide. It's been years since I lived there so things may have changed quite a bit along the lakefront. It used to be pretty scarey. My commutes were in the east 'burbs and none of them are particularly cycle friendly tho relatively flat.

Nashville, where I currently reside is a river town and I commuted for about 4 years here 20 mpd. My commute was ok...all urban w/plenty of space curbside for the most part. In and around Vanderbilt things get a little dicey, especially on 21st Ave where there is NO curbside space AT ALL. East Nashville seems to be getting there as there's a pedestrian bridge w/a bike lane on Shelby ave that wasn't there when I was growing up. But the uptown area is not for the faint of heart or commuting novice...narrow one way streets everywhere. I'm about 35 mi outside of NV now and my commute is 40 mpd(when the factory ramps back up) all rural. Plenty of curbside space and not many cars...I'm very blessed.

Pittsburgh...what can I say? It's a tough town. The cycling community is narrow, but deep. Kind of like the roads and the ruts. There's a sense of pride in being a cycle-commuter or messenger in the 'Burgh. I'd venture the toughest bike messengers in the world all hang out on the South side of Pittsburgh. Where if you have a derailleur you're either a rookie or a p***y. Having only been to SF/Oak once on business I can't imagine the hills being any more difficult there. There's a race on the last Saturday in November called the Dirty Dozen. 13 hills within 5 miles of city center on a 50 mile course. The easiest is 17-18% grade and the most difficult is 37% The race motto is: No money, No medals, no mercy...THAT'S Pittsburgh.