I lived in Chicago for 5 years, San Fran area for 10 years, Los Angeles for 7 years, and Kansas City for about 8 years. I have to say that SF is probably the dirtiest, at least in parts, though Chicago always felt kind of rust-belty in many parts, rather than dirty. In KC, cleanliness tracks money more closely than any other place I've been. The Southwestern cities have always struck me as the cleanest of the places I've been outside of Germany (at least 30 years ago), Switzerland, Canada, and Monaco. Phoenix, Tucson, San Diego, Dallas, San Antonio, Albuquerque.

The other big problem with SF is the parking. Horrendous. And yes, many of the people there do seem to spend a great deal of time in an advanced state of self-congratulation.

Come to vancouver, and you find the west side downtown eerily clean. (East side vancouver is the most ghetto place in canada, literally)

Vancouver is cleaner than Chicago.

I second you on Toronto. I lived there for a few months and was absolutely amazed at how clean it was. Recycling, compost, and trash bins on every corner. Whenever I tell people about Toronto, the first thing I talk about is its cleanliness.