Episode
Inside $2B of Chicago Real Estate: Tommy Choi on Housing, Migration, and Millennials
- Podcast
- The Derivative
- Published
- Jun 11, 2026
- Duration seconds
- 4939
- Processing state
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Summary
Jeff Malec kicks off “Chicago Month” on The Derivative with Chicago real estate powerhouse Tommy Choi of Weinberg Choi. Tommy lays out what really makes Chicago compelling as a place to live and invest—world-class food, underrated beaches, iconic bungalows, and relative affordability, while tackling the tough stuff around crime headlines, taxes, and politics. He breaks down post-pandemic migration, why inventory is so tight, how boomers with 2–3% mortgages and “Bank of Mom and Dad” shape the market, and why millennials are choosing flexibility and crypto over owning. Jeff and Tommy hit on stubbornly high rates, surging rents, condo special assessments, aging buildings, the limits of Loop office-to-resi conversions, and how AI and blockchain might (and might not) change the game. They wrap with a very Chicago detour into best burgers, dive bars, Wrigley in summer, and a few local hacks for seeing the city like a native. If you care about real estate as an asset class, Chicago as a case study in big-city risk and reward, or just want some elite burger intel, this one’s for you. Chapters: 00:00-01:00=Intro 01:01–03:47 = Selling Chicago: Food, Beaches, Weather, Taxes, and Crime Headlines 03:48–15:57 = Inventory Squeeze: Boomers, Millennials, Rates, and the Battle to Buy or Rent 15:58–30:54 = Life as a Top Realtor: Relationships, Weekends, and the Business Behind the Billion 30:55–43:32 = AI, Search, and the Future Home Hunt: How Tech Is Rewiring Real Estate 43:33–59:19 = Commissions, Class Actions, and Blockchain: Cleaning Up the Real Estate Game 59:20–1:07:10 = The NAR Shake-Up 1:07:11–1:22:19 = Chicago Like a Local: Best Burgers, True Dive Bars, Wrigley, Cherry Blossoms, and City Hacks Follow along with Tommy Choi on LinkedIn and X and be sure to check out his website at…