Bill Testa of the Federal Reserve Bank of Chicago has posted an analysis of this subject that raises several interesting ideas. One is that "As the business service center of the Midwest, serving regional markets and industries, Chicago companies’ prospects for growth are somewhat limited." Another is that "globalization of the economy has also brought new opportunities to populous information-based cities like Chicago."
Testa identifies opportunities based on the idea that "expanding global trade in goods, services, and capital requires the complex and specialized functions and industry sectors that are concentrated in large cities, including legal services, logistics, distribution, finance, insurance, business meetings, R&D, and professional business services. Chicago has been developing such sectors almost since its inception."
The question is whether growth in the sectors Testa identifies as opportunities will offset stagnancy or decline in Chicago's traditional strengths.