You don't. In general, whenever you need to go from raster to vector you have to do it by hand. I'd guess that there isn't a program to take bitmap fonts and convert them to TrueType without some, or ...
Pixel fonts represent an interesting era of type design. They were born out of necessity when low-res displays were the only ones around, and have now become a highly niche style of retro nostalgia.
Chicago is part of a family of fonts created by Susan Kare in 1984 for use on the Mac OS. Others are named after cities such as New York and Athens. When Apple began to move away from bitmap fonts, ...