S4 E10 - Taxes, Zoning, And The Chicago Affordability Squeeze . Why Capital is fleeing and how to bring it back to Chicago

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We break down why Chicago’s housing is so expensive. Despite record taxes, the city is at an all-time high in debt. What would it take to attract capital, build more homes, and lower prices? We share data on schools, zoning, conversions, and policy incentives that could restart growth.

• highest taxes paired with large deficits and lender uncertainty
• CTU costs and poor literacy and math outcomes are driving distrust
• capital flight, bank redlining, and private equity debt costs
• stalled office-to-residential conversions and rigid mandates
• aldermanic control and downzoning that choke density and raise prices
• case study on 4330 N California and infeasible set-asides
• renters versus owners, community stability, and wealth
• Northwest Ordinance fees lower legacy owners’ equity
• a practical plan to incentivize office return and revive transit, retail
• three levers for a city: taxes, cuts, or growth, and why growth wins