Policy analysis and ideas on how to make Chicago work better.

Chicago, IL
Joined January 2022
“Candidates are already starting to roll out policy proposals. Voters should watch out for empty promises to build some eyepopping number of units, “streamline” permitting or that old standby: “cut red tape.”
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“Chicagoans should look for candidates that clearly explain the causes of the city’s shortage, and are willing to make specific policy commitments that reflect the scale of the problem we face.“
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“But most importantly, while the politics of zoning and code reform is challenging, the political cost of rising rents is far worse. As Republicans are about to learn in the upcoming midterm elections, the “affordability crisis” is not just a slogan for the campaign trail.”
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Housing and affordability are two of the most pressing issues in upcoming elections, including Chicago’s mayoral race. The upcoming mayor will have to go beyond mere promises of “streamlining” and take tangible steps. citythatworks.substack.com/p…
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“It is also not a mystery why Chicago builds so much less than other cities. To start, our zoning code severely restricts the allowable height and density across much of the city.”
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“Chicago also has some of the highest construction costs in the country, trailing just New York and the Bay Area. That’s a function of a highly restrictive building code that applies limits on wood frame construction and PVC piping.”
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A City That Works retweeted
Come hang out with the City That Works team and meet a bunch of great candidates for Chicago’s School Board this Thursday. Join @biggs4chicago, Anthony Hargrove, and @Isaiah4CPS at the Goose Island Salt Shed Pub from 5-7pm. luma.com/o32e7cw6
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Can Chicago truly be “world-class” when it built less homes than Omaha, Nebraska did in 2025?
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Amongst other major cities in 2025, Chicago ranked dead last in housing construction. For a city of over 2.6 million residents, this ranking is not only an indictment against our cumbersome regulatory environment but threatens our city’s affordability and population growth.
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Chicago must address its building and zoning codes, rework its permitting process, and address high taxes and regulation that have sent development elsewhere. Read more about solutions to our housing crisis: citythatworks.substack.com/p…
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A City That Works’ voter guide for 2026 midterm elections is here. Our recommendations prioritize competent governance and sensible ideas that will steer Chicago in a pro-growth direction. 🏙️ 📈 citythatworks.substack.com/p…
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Make sure you are registered to vote and have a plan in time for the election on Tuesday, November 3rd. Early voting is already open in downtown Chicago. 🗳️ chicagoelections.gov
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With Chicago facing a projected $85.1 million budget shortfall this year, harder decisions will likely be necessary to balance the budget by December, even with the city’s risky decision to refinance bonds last week. citythatworks.substack.com/p…
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“That doesn’t mean refinancing is inherently a bad idea – it’s also bad to keep rolling the dice over and over and hoping for better conditions down the road – but it does mean we’re going to have to look elsewhere to close the budget gap.”
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“The city has already picked nearly all the low-hanging budget fruit; we’ll eventually have to make harder decisions. And the official statement acknowledges that the 2027 budget outlook may negatively affect the ratings on GO bonds and, consequently, STSC bonds.”
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November’s upcoming election for Chicago’s first fully-elected school board can be divided into two camps: those backed by the Chicago Teachers Union (CTU) and those backed by a mix of moderate and business groups. 🧵 citythatworks.substack.com/p…
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“But as the policy demands of the CTU have advanced over the last few years, the politics have shifted dramatically. Most notably, the SEIU, which has long been a close ally of the CTU, is now endorsing non-CTU candidates in a number of races across the city.
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“Today, there is a very big tent of groups working in opposition to the CTU…when you alienate every other political group in town, don’t act surprised when they all end up on the same team.”
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