Hi, Dave. Chicago Tool is one of the many "house brands" of Harbor Freight. They are made in China. Like many items made there, the Chinese will put any name on them if you buy enough.
The quality could best be described as "extremely variable". I have a Chinese drill press that I love. I have had it for years and it has really served me well. But I also know that the next Chinese tool that I buy could cause me nothing but trouble.
Personally, I would not buy a Chinese tool that I expected to use often and had to depend on. At the same time, if I wanted a cheap tool that I would rarely use and just wanted something cheap for occasional use, or if I wanted to try out a tool to see if I would use it often enough to justify spending 3 or 4 times more for a good tool, the Chinese tools make sense. There are some American "brand name" tools that fit in this category also, like Black & Decker, so the Chinese don't have an exclusive on cheap tools with variable quality.