I co-founded and co-managed a decent-sized consulting practice that served NYC, Chicago, and SFBA simultaneously.

Chicago is, I think, a better city to consult from than SFBA is (it's close, though). There are more opportunities to do contract dev for tech companies in SFBA, of course, but contracting jobs in SFBA tend to allow remote workers. Meanwhile, the business community in Chicago is much more diverse, so if the kind of work you do is amenable to solving problems that "Fortune 500 companies that don't employ 1,000 software developers" have, Chicago is full of prospects.

Chicago consultancies won't pay you market rate either