Best free alternatives to

Chicago

Apple released Chicago in 1984 with the original Macintosh, designed by Susan Kare as a single 12-point bitmap for menus, title bars and dialog boxes. Working within a low-resolution screen, she built the letters from horizontal, vertical and 45-degree strokes only, which gives the face its blocky, heavy, slightly squared character. Bigelow & Holmes drew a TrueType outline version for Apple in 1991, and the design returned on the first iPods in 2001. Chicago was never sold as a retail family and no longer ships with macOS. These free typefaces work the same squared, heavy sans register without the hunt for an old system file.

The closest font to Chicago
More fonts similar to Chicago
The quick brown fox jumps over the lazy dog
The quick brown fox jumps over the lazy dog
The quick brown fox jumps over the lazy dog
Pairings

Display + body that work together

The shape of a working week
The display sets the register; the body follows through. When both halves of a pair pull in the same direction, the design disappears and the words come forward.
Modern · Editorial Chakra Petch + Crimson Pro
Headlines that read at a glance
Two thousand years of letterforms boil down to a handful of decisions — width, weight, proportion. Pick a pair you trust, and let the rest take care of itself.
Editorial · Modern Playfair Display + Chakra Petch
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FAQ

Common questions about Chicago alternatives

Is Chicago free?
No — Chicago is a commercial typeface from Apple. Chicago is Apple's proprietary system font; it was never sold as a retail typeface and is not bundled with current macOS, so there is no official download. The closest free alternative is Chakra Petch, available on Google Fonts.
What font is similar to Chicago?
Chakra Petch is the closest free match. A squared sans whose corners are cut on the diagonal rather than curved, echoing the straight-and-45-degree construction Kare used for Chicago's bitmap. Its heavier weights carry a similar blocky presence, though it is cleaner and more condensed, with a technical rather than pixel-era feel.
Can I use Chakra Petch in commercial projects?
Yes — Chakra Petch is published under a free license on Google Fonts and can be used in commercial work. Confirm the license text at the source before shipping.