Plus, Chicagoans struggle with housing ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌ ‌
Wednesday, May 20 

Your Daily Guide

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

An aerial view of a neighborhood

Homes on the South Side. (Brian Cassella/Chicago Tribune/Tribune News Service via Getty Images)

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.

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.

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.

American Writers Festival poster with colorful text and graphics. Event on June 6-7, 2026, lists authors like Reza Aslan, Susan Orlean. Free literary event.

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 Chicago's 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]

PODCAST

Pritzker Disses Johnson…Again. Plus, New Northalsted Bar, and Chicago’s Favorite Rivalries

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 🎧]

A parking meter on a sidewalk of a street with cars and bikes

Chicago drivers hate to see a Chicago Parking Meters LLC pay station. (Terrence Antonio James/Chicago Tribune/Tribune News Service via Getty Images)

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]

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What To Do

Wednesday, May 20

Thursday, May 21

More Chicago Events
Display Ad: Free and Independent Exhibit at The Newberry

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…

— Michelle Navarro

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