
City Cast Chicago
🚙 Parking meters to be sold … again.
May 20, 2026 · — Michelle Navarro
Love is in the air, Chicago. Or at the very least, in this Jewel Osco parking lot. Someone captured a couple holding hands and skipping to the grocery store. A true Chicago love story.
Now, on to today’s headlines!

Today's Big Story

Affordable Housing in Chicago
“Chicago is in the midst of an affordable housing crisis that has been building for a long time,” a letter from the Department of Housing states. There are 100,000 fewer affordable homes than there are households in need.
So what’s going on with the city’s stock of affordable housing?
CHA Waiting game: The Chicago Housing Authority is the city’s largest landlord with more than 21,000 units. But about 18% of sites are vacant due to rehabilitation needs. Meanwhile, Chicagoans can be stuck on the waitlist for years. The wait for public housing may get longer once the federal government’s Emergency Housing Voucher Program runs out of funds this year, potentially affecting more than 1,100 households in the city.
- Remember when an alder waited nearly 30 years to make it to the top of the list?
Relocations: Waitlists for CHA relocation requests due to safety concerns are almost as long. Residents with disabilities, experiencing domestic abuse, or facing health issues at their current unit are struggling to be transferred into safe, accessible housing.
Leadership drama: Mayor Brandon Johnson wasn’t thrilled about the April appointment of CHA's new permanent leader, Keith Pettigrew, citing issues of transparency. The agency was without a leader for a year and a half.
More accessible units: A city panel just agreed to a $2.25 million settlement in a lawsuit brought by a disability advocacy organization claiming Chicago failed to build enough affordable housing for people with disabilities. The agreement calls on the city to build or rehabilitate 2,000 new accessible, affordable units.
Affordable housing developments in the works: CHA isn’t the only agency that can create affordable housing in Chicago. Many organizations are taking matters into their own hands.
- The Missing Middle Initiative aims to revitalize neighborhoods. The Far South Community Development Corporation plans on transforming vacant lots in Morgan Park into three-flat residential buildings this fall.
- Faith-based groups are creating housing on underutilized land, calling it “Yes, in God’s Backyard.”
- This developer’s Garfield Park units are nearing completion.
- A report on housing near transit hubs shows progress five years after the city signed off on the policy.
Online housing resource: An online affordable housing portal pilot could grant residents access to a network of affordable units. City council is set to vote on the ordinance today.
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Chicago’s Free Literary Weekend featuring Award-Winning Writers
Bestselling storytellers come together for the American Writers Festival, June 6–7. Presented by the American Writers Museum in partnership with the Chicago Public Library, the festival features in-depth with writers across genres, plus workshops, storytimes, book signings, and family-friendly activities for attendees of all ages.
Events run from 10 a.m. to 5 p.m. both days, with programming at the American Writers Museum on June 6 and Harold Washington Library Center on June 7. Learn more at AmericanWritersFestival.org.

What's CITY Talking About
Two Alders File Suits — One Against the City, One Against the Feds
Ald. Jessie Fuentes (26th) is suing the federal government for $100,000 after federal immigration agents shoved and handcuffed her in a Humboldt Park hospital in October. At the time, footage of the incident went viral. Fuentes says she’s dealing with “physical, psychological, and emotional injuries.” [Tribune 🔒]
Meanwhile, Ald. James Gardiner (45th) is suing the city for $1 million, nearly a year after ethics violations against him were dropped. In 2023, the Chicago Board of Ethics ruled that Gardiner had committed 10 violations, including ticketing a critical constituent for overgrown weeds, and fined him $20,000. [Block Club]
New Latino Northalsted Bar. Plus, Pritzker Disses the Mayor
A new bar is celebrating Chicago’s queer Latino community in Northalsted. On today’s podcast, we break down the latest. We also discuss the drama surrounding the Bears’ pending stadium and our favorite rivalries in the city. [City Cast Chicago 🎧]

Parking Meters to Be Sold. Again.
The private consortium that owns most of Chicago’s parking meters is set to transfer ownership — and hundreds of millions in annual revenue — to a New York investment firm. The final deal is subject to City Council approval. [CBS Chicago]
- Earlier this year, Mayor Brandon Johnson floated a $3 billion proposal to buy the meters back. But city experts said it was unfeasible. [City Cast Chicago 🎧]
- Good thing we only have 57 years left on one of the city’s most hated deals 😬 [City Cast Chicago 🎧]

What To Do
Wednesday, May 20
- 🏀 Sky Home Opener | Wintrust Arena | South Loop
- 📽️ “UnBroken” screening | Wayfarer Theater | Highland Park | Free
- 🌳 Woodland Habitat Restoration | Skokie Lagoons | Free
- 🧵 Queer Stitch Night | Gerber/Hart Library and Archives | Rogers Park
- 🔭 Free Admission | Adler Planetarium | Museum Campus
- ⚾ Cubs vs. Brewers | Wrigley Field
- 🔪 “Hookman” | Bramble Arts Loft | Andersonville
Thursday, May 21
- 🎷 Red Line Jazz Project | Howard Station and Pottawattomie Park | Rogers Park
- 🏆 Partners in Dignity Soiree | Venue West | Near West Side
- 🎤 Kuumba Soul | DuSable Museum | Washington Park | Free
- 🖼️ Studio Sale | Arts of Life | West Town
- 🥊 Boxing Show | Columbus Park | Austin | Free
- 🌃 Chicago Astronomer | Horner Park | Irving Park | Free
- 📽️ “EXistenZ” | Logan Center | Woodlawn | Free
- 🅱️ Auntie Shelia’s Bingo Night | Da Book Joint | South Shore
- 🍽️ Neighborhood Picnic and Art Opening | National Public Housing Museum | Little Italy | Free
- 🖼️ Free Admission | Art Institute | Loop
- 🖼️ IAM Celebrating | Intuit Art Museum | West Town
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The Newberry Commemorates America at 250
Chicago’s Newberry Library is commemorating the 250th anniversary of the signing of the Declaration of Independence all year long.
Visit our current exhibition, Free and Independent: The Declaration of Independence and the Words That Made the United States, which includes a July 1776 broadside copy of the Declaration and John Jay’s handwritten manuscript of the Federalist No. 3. Then visit our reading rooms to view Thomas Jefferson’s annotated copy of The Federalist and George Washington’s diary.
Learn more about our 250 commemoration on our website!
Do you have anyone in your life that you’d trust not to fall off a floating bike track? If so, you should participate in the Chicago Red Bull Spin Off. Chicago-related costumes are encouraged!
Also, thank you to a reader who noticed that we misidentified a NASCAR vehicle in yesterday’s newsletter. Neither Emmi or I can drive…
Free · Daily



