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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?

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Did you ever extract the Chicago font? – user41226 Feb 5 '13 at 22:10
    
Yes, and it's awesome. – Daniel Feb 5 '13 at 22:13
up vote 26 down vote accepted
+50

The last version of the OS to use this font as default was System 7.

For Mac OS 8, Apple decided to discard this wonderful part of their brand’s identity, and commissioned David Berlow of the Font Bureau to design Charcoal.

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

  1. Download the System 7 disk image from Apple for free here
  2. Unpack System 7.0.1.smi.bin with "The Unarchiver.app" (free on the App Store here)
  3. Convert System 7.0.1.smi to a dmg image using Disk Utility using the menu item 'Images > Convert'
  4. Open the resulting System 7.0.1.smi.dmg and get the Fonts.image inside
  5. Convert Fonts.image to a dmg using Disk Utility
  6. Open the resulting Fonts.image.dmg
  7. Enjoy your retro goodness.

Chicago OSX

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Using the font as the system font and including it with the OS are two different things, although obviously the second is a necessary condition for the first. – Daniel Jul 30 '12 at 4:03
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Yep, saw my error and updated the post. I also found a way to extract it from System 7, so I'm adding that to my answer too. – Tyr Jul 30 '12 at 4:24
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Awesome step-by-step instructions. This answer rocks! – Daniel Jul 30 '12 at 13:55
    
Part of the reason for the abandonment was display technology - Chicago was designed to be easy to read on chunky screens. In the days of Retina displays, not needed as much. It did have a bit of a revival on the big white iPods though, for the same reason (chunky pixels in the display). The "displays are better" argument can explain why it's not the system font, though not why it was removed altogether. I just installed the typeface on my Mavericks box. I still see this typeface in use, asia/Japan mostly. – Rich Homolka Jan 23 '14 at 17:49
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I think these are the clearest instructions I've ever seen on the internet. Thank you! – jmtroos Feb 26 '14 at 12:55

You can get a copy of a TrueType Chicago font here:

http://www.fonts101.com/fonts/view/Standard/21727/Chicago

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4  
Is this legitimate? I don't see any license terms. – Daniel Jul 29 '12 at 4:03

Oddly, the Krungthep font currently supplied with OS X, while a Thai language font, has the latin characters drawn in Chicago.

I found this out here while trying to figure out why the Krungthep chosen by a non-technical friend for the headings of her website design looked so familiar...

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An update for El Capitan:

OS X 10.11 has a new Disk Utility that can't do what the current best answer suggests. We need to adjust what we do on Steps 3 and 5.

Once you've used Unarchiver to unpack the .bin file from Step 2, jump into Terminal (I'm going to assume basic familiarity with how to use the terminal) and issue the following the command:

hdiutil convert System\ 7.0.1.smi -format UDRO -o sys7.dmg

This will give you a mountable image for System 7 named sys7.dmg. Mount it and copy the Fonts.image out to, say, your desktop. We need to do the same thing again on this fonts file.

hdiutil convert Fonts.image -format UDRO -o fonts.dmg

Voilà! We now have a modern, mountable disk image called fonts.dmg. All System 7 fonts will be inside, including Chicago. Double click a font to install it on your computer.

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