Your Guide to May 2026 in Chicago

Are more regulations coming to the city’s scooters and ebikes? Following several fatal accidents involving minors, lawmakers have proposed a bill to add age and road restrictions for the state’s growing number of motorbikes, e-bikes, and scooters. Plus, Chicago is ranked one of the worst cities for mosquitoes, and what would you copy from other cities? Good News: Save Our SNAP Block Party Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 If you enjoyed today's interview with Director at Springfield Convention & Visitors Bureau, Scott Dahl, supporting Enjoy Illinois, learn more here. Learn more about the sponsors of this May 12 episode: Window Nation Visit Bloomington Randolph Street Market Griffin MSI Newberry Library Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

What sets Chicago brick apart? Why are bald eagles returning to Chicago? What would you wait in line for? City Cast Chicago contributors Leigh Giangreco and Al Scorch join us today to break it all down. Also, we hear a poem from YOU! Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 11 episode: Window Nation Visit Bloomington Randolph Street Market Griffin MSI Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

Why did Mayor Brandon Johnson go to Springfield? Will state police actually investigate the killing of Silverio Villegas González by ICE last year in Franklin Park? We’re answering these questions with Borderless Magazine’s Katrina Pham and WTTW’s Heather Cherone. Plus, eaglets have been spotted on the South Side, and Obama Presidential Center’s tickets are selling out fast. Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 8 episode: Illinois Solar Energy Assoc. Enjoy Illinois TimeLine Theatre Co Window Nation Newberry Library Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

Happy Teacher Appreciation Week! Earlier this year, we visited the Carole Robertson Center for Learning at their Albany Park site to talk to teachers and students about why after-school programs are critical to families across the city. On the center’s 50th anniversary, we wanted to revisit the conversation we had with these Chicago kids about what they want adults to know. Good news: Emmett and Mamie Till-Mobley House Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 7 episode: Illinois Solar Energy Assoc. Enjoy Illinois TimeLine Theatre Co Window Nation Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

In April, a federal judge ruled the Trump administration could not cut Medicare and Medicaid funding to hospitals providing gender-affirming care to minors. Host Jacoby Cochran, contributors Anna Deshawn and Brandon Pope discuss why Chicago hospitals have yet to reinstate their services for transgender youth. Plus, lawmakers want gun manufacturers to pay for gun violence, and Chicago’s summer festival season is right around the corner.  Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter.  Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 6 episode: Illinois Solar Energy Assoc. Enjoy Illinois TimeLine Theatre Co Window Nation Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

A new report shines light on how immigrant families in Chicago continue to suffer months after the height of Operation Midway Blitz. Many families are struggling to find consistent work, are behind on rent, and are at risk of eviction. Host Jacoby Cochran and creative producer Michelle Navarro look over the report’s findings. Plus, it seems that May Day went down pretty smoothly for CPS, and we’ve got some of our favorite places to take the kiddos in our lives. Good News: "Aged Well" Documentary Screening Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 5 episode: Illinois Solar Energy Assoc. Enjoy Illinois TimeLine Theatre Co Window Nation Newberry Library Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

May flowers are blooming all around us as summertime Chicago is on the horizon. We’ve got your guide to what’s happening in Chicago this month — rain or shine. Host Jacoby Cochran, creative producer Michelle Navarro, and audience development manager Chima Ikoro have events to look forward to, tips for May, and news stories to watch. Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 4 episode: Illinois Solar Energy Assoc. Enjoy Illinois TimeLine Theatre Co Window Nation Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

Property tax bills remain a headache for thousands of Chicagoans, as tech issues continue to delay bill arrivals. We ask the Tribune’s A.D. Quig and Axios Chicago’s Monica Eng, who is to blame for this decade-long snafu. Plus, prosecutors weigh possible Midway Blitz investigations, Illinois farmers are struggling, and Unity Day 2026 is back in Englewood. Good News: 1920s Chinese jazz cafe, “Oh, Mary!” Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this May 1 episode: Steppenwolf Theatre Paramount Theatre Visit Bloomington TimeLine Theatre Co Newberry Library Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

Earlier this year, the co-owner of the restaurant Warlord, Trevor Fleming, was arrested and charged with sharing explicit images of a woman without consent. We discuss what some employees have called a culture of abuse and the impact it has had on the restaurant since. Host Jacoby Cochran is joined by contributors Leigh Giangreco and Al Scorch. Plus, the DMV continues its modernization effort, and we want to know which Chicagoan deserves a big-budget biopic. Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter. Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this April 30 episode: Steppenwolf Theatre Paramount Theatre Visit Bloomington TimeLine Theatre Co Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE

After years of advocacy, Mayor Brandon Johnson signed the Peacebook Executive Order. Developed by the youth-led organization, Good Kids Mad City, this order establishes the city’s first permanent year-round youth peacekeeping program. Host Jacoby Cochran is joined by contributors Brandon Pope and Anna Deshawn. They discuss details of the executive order, the new lesbian-owned bar Fathom, and the Chicago Critics Film Festival. Good News: First Friday Music Series Want some more City Cast Chicago news? Then make sure to sign up for our daily newsletter.  Follow us @citycastchicago You can also text us or leave a voicemail at: 773 780-0246 Learn more about the sponsors of this April 29 episode: Steppenwolf Theatre Paramount Theatre Visit Bloomington TimeLine Theatre Co Become a member of City Cast Chicago. Interested in advertising with City Cast? Find more info HERE