I'm running Mountain Lion on a mid 2011 MacBook Air.
I'd love to be able to set type in the oldest Macintosh system font, Chicago. Is this font included anywhere in OS X Mountain Lion? If not, what is the most recent Macintosh operating system to include the font, and can the font be purchased anywhere?
Best Answer
The last version of the OS to use this font as default was System 7.
Apple actually released System 7 for free download here. Conceivably you could load up System 7 in an emulator like Sheepshaver and get the font out somehow. Or unpack the system images provided by Apple, though I don't know which software you would need for that.
Apple abandoned Chicago as of OSX, as evidenced by the outrage here. Locally, I can buy an original iMac running OS 9 for 50 EUR. So you could buy one of those and transfer the font :-)
UPDATE: extracting Chicago from System 7