The city and Illinois also have massive unfunded public-pension liabilities, which could force them to raise property- or income taxes in the years ahead. Chicago already has the second-highest residential property taxes in the country, according to research firm Green Street Advisors.

“The primary reason that Chicago is struggling from an investment-sales perspective is the outlook for higher taxes in the future,” said Dave Bragg, a managing director at Green Street.

The city has ample land and faces fewer restrictions on new construction than does the Bay Area. This has helped keep housing affordable but hurts owners.

The number of tech job openings in Chicago grew 22.7% in November compared with a year earlier, according to Glassdoor, as more employers look for affordable alternatives, analysts say.