
City Cast Chicago
✅ Your guide to June in Chicago
May 29, 2025 · — Emmi Mack
Hey Chicago! Listen up! You’re going to want to save this newsletter — bookmark it, star it, whatever — because it is jam-packed with June recs. From Ribfest to blues jams, from Pride-a-paloozas to the Puerto Rican parade, there is lots going on this month. We’re breaking it all down here and on the pod. So pay attention.


What Chicago's Talking About

New Illinois Transit Plan Does Not Address Fiscal Cliff
State lawmakers unveiled a bill days before the end of the legislative session to replace the Regional Transportation Authority, which oversees CTA, Metra, and Pace. A new Northern Illinois Transit Authority would create a universal fare system and oversee big projects, but the measure does not address the looming $770 million fiscal cliff that threatens to upend 40% of CTA service. [WTTW]
- Related: What’s the deal with the CTA’s fiscal cliff? [Hey Chicago 💻]
Pope Leo Celebration Mass to Be Held at Sox Park
On June 14, Rate Field will host a mass in honor of Chicago’s own Pope Leo XIV. It’ll be a celebration, too, with music, film projections — and a video message from Pope Leo himself. Information on tickets will become available soon. [NBC 5]
South Side Concrete Cadillac Gains New Attention
The 1957 Cadillac DeVille encased in concrete is art. “Concrete Traffic,” was created by Wolf Vostell in 1969 and moved into a University of Chicago parking garage in 2016. Now, amid renewed attention on social media, a conservation team is working on a book about the avant-garde sculpture. [Block Club]
Sponsored Content

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, Tony Danza, Whitney Peak, William Harper Jackson, and more. Discounted hotel rooms available through June 1. Choose a weekend, buy a pass.

Neighborhood Shoutout
We love our Neighbors for so many reasons — they help us keep City Cast Chicago going! But also because they come through with the recs. This week, we’re spotlighting a Neighborhood Shoutout from Elizabeth S. of West Town.
- Elizabeth S. is shouting out Chi-Latin: “Chi-Latin is a local restaurant owned by a friendly and fantastic chef who fuses the diverse cuisines of the Américas into delicious dishes. Good drinks and all-around good vibes.”

What To Do
Thursday, May 29
- 🧶 Crafty Kids | 4:30-5:30 p.m. | Free | Bronzeville
- 🍄 The Shroom Room: An Interactive Mushroom Workshop | 6 p.m. | $10 | North Lawndale
- ✍️ Chicago’s Youth Poet Laureate Ceremony | 7-9 p.m. | Free | Loop
- 🇯🇲 Reggae Express ft. Hurricane | 7-10 p.m. | $15 | West Loop
- 🎤 Raq Baby | 7-10 p.m. | $30+ | Hyde Park
- 🤼 OnlyWrestlers Chi-Town Beat Down | 7:30-10:30 | $39 | Albany Park
- 👠 Drag Trivia Thursdays | 7 p.m. | $71 dinner package | Nothalsted
- 🍷 Pretty Girls Love Thursdays | 9 p.m. to 2 a.m. | Free-$15 | West Loop
Friday, May 30
- 🌭 Windy City Hot Dog Fest | 4-10 p.m. | Free | Portage Park
- 🎉 Do Division Street Fest | 5-10 p.m. | Suggested Donation | West Town
- 🏺 Wheel Throwing For Beginners (BYOB) | 5:30 p.m. | $40+ | Pilsen
- 🥃 Spirits & Spice Chicago Whiskey Experience | 5:45 p.m. | $13 | Streeterville
- 🍷 Wine Fest on the Beach | 6-9 p.m. | $42+ | North Avenue Beach
- 🎤 The Weeknd | 7 p.m. | $65+ | Soldier Field
- 🌟 Underscores B2B Umru | 10 p.m. | $25 | Wrigleyville
- 👑 The Queens: 4 Legends, 1 Stage | 8 p.m. | $97+ | United Center
- 🎱 Music Bingo | 8 p.m. | Free | Wrigleyville
- 🕺🏼 Feed Me | 9 p.m. | $37 | Wicker Park
- 🎵 La Bamba / Tiwa Bleu | 11 p.m. | $27 | Ukrainian Village
😉 I’ll catch you out on the town this June. Don’t forget about those new speed cameras!
Free · Daily

