
City Cast Chicago
🛒 Maxwell Street is back. Sort of.
May 14, 2025 · — Emmi Mack
Hey there! No pope buddies have reached out with Dolton goss — yet. But I believe in you guys. Our lines are open. At least the Sun-Times came through with some info on Pope Leo’s Florida brother. More on that below.
🐻 Also, for those of you still invested, the new season of The Bear drops June 25. All 10 episodes at once.

What Chicago's Talking About

Block Club Sues ICE
Block Club Chicago, a nonprofit news organization we cite often, is suing
U.S. Immigration and Customs Enforcement and Homeland Security for violating the federal Freedom of Information Act. According to Block Club, ICE never revealed who was arrested in raids or where those detainees were taken. [Block Club]
- Related: Block Club is not the only entity suing ICE. [City Cast Chicago 🎧]
Tent Encampments Cleared at Gompers Park
The final tents at Gompers Park were removed Monday morning to make way for park restoration. Many people living in the tents were moved ahead of the construction, but not all. Chicago Park District Superintendent Carlos Ramírez-Rosa says the city is working with those remaining to move elsewhere in the park. [ABC 7]
Pope Leo's Bro is Big-Time Trumper
Up until Monday, Pope Leo XIV’s oldest brother Louis Prevost’s Facebook profile was full of slurs about Democrats. Shared posts from the Floridian include a caption calling Nancy Pelosi a “drunken c***” and expressed that “anti-Trump Democrats” be “arrested and tried.” Posts of that nature date back for years. [Sun-Times]

Buying a Bike in Chicago: 101
As the weather warms up in Chicago, it’s time to get biking. Liam Ouweleen of The Recylery, a bike repair co-op in Rogers Park, shared tips with City Cast Chicago for bike shopping and bike maintenance. Plus, how to navigate the city street safely, bike lane or not. [City Cast Chicago 🎧]
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Don’t miss the new Williamstown Theatre Festival
Adventurous theatre lovers are gathering amongst the Berkshire mountains for the boldly reimagined Williamstown Theatre Festival, including a world premiere by Jeremy O. Harris, Tennessee Williams plays starring Pamela Anderson, Whitney Peak, William Harper Jackson, and more. Discounted hotel rooms available through June 1. Choose a weekend, buy a pass.

Neighborhood Shoutouts
Time for your Neighbor shoutouts! Each week, we hear from some City Cast Chicago Neighbors about their fave local companies or organizations.
- Mike M. of South Loop is shouting out Chicago Movie Tours: “Chicago Movie Tours offers an amazing tour of the Art Institute called ‘The Art of Ferris Bueller.’ So fun!”
- April D. of Lincoln Park is shouting out Simmons Center for Global Chicago: “[It’s] connecting globally engaged nonprofits with a footprint in Chicago.”
- Jeff S. is shouting out Friends of the Forest Preserves: “Outstanding free events and volunteer opportunities throughout Chicagoland's most underrated asset, our forest preserves.”
Become a City Cast Chicago Neighbor to share your own shoutout in this very newsletter — and on the podcast!

What To Do
Wednesday, May 14
- 🧶 Committed Knitters | 11 a.m. to 3 p.m. | Free | Hyde Park
- 🎶 Groove with DJ Kosmo | 5-8 p.m. | Free | Loop
- 🍷 Wine-Not Wednesday | 6 p.m. | $12.50 | Loop
- 🎬 “A Life Unwritten” | 7 p.m. | $25.96 | Streeterville
- 🎵 Anna B Savage | 8 p.m. | $33 | Lincoln Square
- 🤣 Mother!: a night of comedy & revelry | 7-8:30 p.m. | $16.24 | Humboldt Par
- 🎤 Luya #59: poetry & arts open mic | 7:30-10:30 p.m. | $5 | Humboldt Park
Thursday, May 15
- 📖 “It’s a Mood” book signing | 5:30-7:30 p.m. | Free | Lincoln Square
- 🍾 Spirits & Spice | 5:45-6:15 p.m. | $12.51 | Near North Side
- 🏳️🌈 LGBTQ+ Networking | 6-9 p.m. |$17.85 | River North
- 📚 Poetry Reading | 6-7:30 p.m. | Free | Near North Side
- 🎤 Grown Folks Stories | 7-9 p.m. | $13.95+ | Hyde Park
- 💕 POC Speed Dating | 7-10 p.m. | $15.71+ | Avondale
- 👑 Beyoncé: Cowboy Carter Tour | 7 p.m. | $150+ | Soldier Field
Between Maxwell Street and National Vintage Store Day, it’s a big weekend for second-hand shopping! Check Hey Chicago tomorrow for a closer look at the city’s vintage scene 😘
Finally, say hey to our newest Neighbors: Jenesia P., Susan S., Juan Sebastian A., and Maura N.!
Free · Daily

