As an exercise, I tried making a font inspired by trying to "warm up" the outline version of the classic Mac font Chicago, which Kris Holmes and Charles Bigelow created from the original bitmap version by Susan Kare. This is not to say I traced anything, or reused any .ttf files. I couldn't even find a .ttf of chicago: I worked by eye from some sample images of the alphabet, and the bitmap originals.
Despite Chicago's eye-catching stylistic consistency, (at least in my amateurish opionion) I've never really cared for the cold geometricness of it at large sizes, and it seems to be only increasing in popularity lately. I just saw it on an outdoor sign when combinator gave me a ride home the other night. I do sort of like the peculiar v, w, x, and f, though, and I figured with a little less stick-up-assery, I could actually like it. Thus, Evanston. It's still very sketchy at this stage, though. The a is a little overcooked, and so too may be the bdpq. The x is all wrong. On the other hand I like the f, k, and s very much.
The weight is too much to count as a counterpart to chicago, although I imagined I might try to actually do a lighter version anyway, that is, even lighter than chicago. I think I'll call this the black version, call the chicago-balancer bold, and maybe try to do a book weight if I feel like sinking that much time into it.
For even further comparison, Chica Mono is a monoline sans-serif inspired by Chicago. I'm definitely planning to keep my design modulated, but it's pretty nice!