Pitfalls of Chicago style? Chicago vs. A.P.

It has been some time since I have worked with Chicago style and now I’m faced with an assignment that uses Chicago instead of A.P. or Bluebook. I’ve got the massive tome in front of me, but I’m wondering whether anyone has pointers on “don’t miss this quirk of Chicago” style or some major differences between Chicago and A.P., for example.

Any suggestions?

Biggest thing is the serial comma: Chicago Manual uses is; AP does not.`

Yep, serial comma is the biggest one. AP Style also insists on hyphenating teen-ager, although most newspaper stylebooks overrule that quirk.

It also has some odd rules on the usage of apostrophes. For example (and I don’t have the Chicago Manual of Style at hand to compare, so somebody please check for me), AP Style says:

It also adds only an apostrophe for singular proper names ending in “s,” so it’s “James’ book” instead of “James’s book.”

Chicago Style says to spell out numbers up to ninety-nine.

Thanks for the tips! I’ll definitely read up on those points.

I’m going to jump on/revive this thread. Are there any websites or books (or whatever) that compile neatly the differences between Chicago and AP?

The 2005 AP Stylebook doesn’t hyphenate teenager. The entry says, “No hyphen is a change in AP style,” so it most likely changed with that edition.

Finally!

I am somewhat disappointed this thread was not about pizza.

I am somewhat disappointed this thread is not about a new gangster-themed side-scrolling videogame from Activision.

What does Chicago say about Web site/website?