Looking for Chicago Italic Font

Question

Aloha gang:
As you know, Pages only has our good friend Chicago font in the regular face.
I have tons of prior work/logo/webpages made via Appleworks using the italic & bold versions. Spent several hours googling but not finding.
DOES ANYBODY KNOW WHERE I CAN GET THIS FONT ???
  Mac OS X (10.4.6)  

Answer 1

Hullo Don:
Actually I don't have Chicago in my font collection with Pages at all. From your post I assume that the regular version must be included with the "Classic" version of Mac Os, which (not having any legacy files) I have chosen not to load.
You would seem to be correct in your observation that Pages will not synthesize (or "fake") italics by simply obliquing the regular font, whereas Appleworks would seem to do this. I tried Andale on both to check.
A comprehensive selection of "Chicago" fonts can be found on www.Fonts.com, however. If you know the font, you will recognise whether these include your old friend, or are simply a different collection under the same name. I suspect, however, that what was included in Os 9 might well have been just a subset of the complete family, as bundled fonts not uncommonly are.
Notwithstanding, the genuine italics (which will be better designed, from a typographical standpoint) may not completely answer your need. If your hope was to import Appleworks including Chicago italics into Pages, the italicised fonts may not necessarily be recognised even if you bought and loaded and installed the true italic version. Having no Appleworks documents, I am unable to experiment with whether Pages will recognise the italicised font as belonging to a Chicago font it knows. If it does, the import would probably not be italicised - but if you had the genuine italic font you could then reformat the original obliqued font with it
On the other hand, if the currently available set is the one you know, and you installed it in your Pages accessible collection, you could "paste and match style" (having established a style in Chicago Italic) into Pages documents. The result, if the fonts indeed match, would not be identical - but would match the style of your previous documents except with the typeface discernibly refined. A true italic font is drawn afresh, with further adjustments to the regular font than just obliquing it. Sometimes it is altogether different, too; e.g., Didot - or most distinctly of all, Joannah.
I also recall, from a post many moons ago, that there are also third party font manipulation programs that will allow you to synthesize an italic font from a regular one. Even these, though, might pose some problems with the font names clashing. The alternative is that Pages would fail to recognise the obliqued regular font, and return a "could not open ... missing font" message or the like.
The post I distantly recall did encounter and resolve this problem. As I recall, it was found necessary to rename the generated italic font to distinguish it from the original.
Be prepared, then, for a bit of tweaking, even if you do find the Fonts.com collection includes what you want. Otherwise, maybe another poster might remember the font manipulation program that was involved in the post I am sorry I dimly recall, or otherwise be familiar with a suitable font manipulation program to which to refer you.
Your best bet might well boil down to i) whether the currently available Chicago italic is the font you're after, and ii) whether some typographical upgrading of your previous materials is better or worse for you than minutely conserving their original appearance.
The fact that fake italics were ever considered acceptable in the first place suggests that few might notice the difference, other than in examples like the above. But (IMHO) Pages is pernickety just where it should be. It pays scrupulous regard to typography - which is really the root of its charm.
Happy hunting and good luck.
iBook G4   Mac OS X (10.4.5)