I heard back from UChicago this morning-
“For admissions purposes, we do require documentation of satisfactory completion of a secondary education, which can include a GED. I am not sure of all community college requirements, and you may have looked into this already, but in order to be formally enrolled as a degree seeking student rather than a student taking classes, they may want you to show formal completion of secondary education as well. While you could then technically applying as a first year applicant after receiving a GED, I think that the benefit of starting at a community college would be the opportunity to experience the classroom setting in a preparatory environment, and also to beef up your academic record. The other thing I want to highlight is that for UChicago, and for any liberal arts programs that you may be considering, you will be most successful if you are able to demonstrate documentation of more well-rounded preparation. Classes in the programming engineering field are good, but I would also encourage you to take math classes, and English or history classes as well. On our website we have a section called Preparing for College, which provides some suggestions (not requirements) for students to think about what a preparatory education might look like. As a transfer student, it’s not so much the number of years here as it is the variety of subjects that we’re looking at. Different schools would have different requirements, and as you look into different schools and different programs, you may find too that maybe you want something more technical, or to go to a more traditional engineering school rather than a liberal arts education. I encourage you to talk to different admissions offices, and see how different offices do things.”
I’ll compile a list of schools I’m interested in and try to work my CC classes around the shared requirements between schools.