Straight Up Chicago Investor

Episode 435: 36th Ward: Future of Chicago with Alderman Gil Villegas

Feb 26, 2026
Guest
Gil Villegas
Gil Villegas, alderman of Chicago's 36th Ward and chair of the city's Economic Capital and Technology Committee, talks zoning and affordable housing policy. He discusses using zoning changes to create community wins, cutting red tape with tech and RFIs, organizing council action on the budget, and why he withdrew from the Northwest Housing Ordinance. He ends with a bullish vision for Chicago's future.
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INSIGHT

Pragmatic Upzoning Balances Revenue And Community

  • Gil Villegas supports upzoning when it creates a dialog that balances developer viability and community needs.
  • He frames development as necessary revenue for city services and accepts negotiated affordability to keep owners financially solvent.
ADVICE

Come Ready To Negotiate And Pencil Conservatively

  • Developers should come prepared to negotiate and expect community feedback at multiple meetings.
  • Villegas recommends penciling proformas at reduced heights (e.g., four vs five stories) so projects remain feasible after compromises.
ADVICE

Use Tech To Make Permits Predictable

  • Use technology to add transparency and predictability to permits so developers can plan phasing and financing.
  • Villegas suggests RFIs, pilot projects, and AI to flag missing paperwork and assign a single project contact.
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