Chicago, IL: -27.7% Return on Investment (2011) Chicago is another market area that experienced a dramatic escalation of market values from the real estate bubble.  With high rates of regulation and taxation, Chicago is an intrinsically difficult place to invest.  Historically, values have been very high relative to rents and the restrictive land use laws […] The post #73 – Market Predictions for Chicago, IL in 2011 first appeared on Jason Hartman.