I'm from Chicago suburbs, but worked in the city this summer. I agree 100% with Thiel. I'm trying _very_ hard to not have to work in the city when I graduate in December. I believe the passion just isn't here from the small sample of software engineers that I interacted with. I might be extremely naive to say that. I think evidence would support my theory such as there not being very many interesting startups in Chicago. Only a select few that I've heard of that I would want to work at. Chicago seems to be dominated by Finance.