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City Cast Chicago

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.

Podcast Player: "Your Guide to June 2025 in Chicago"

What Chicago's Talking About

A CTA bus passes by Rate Field.
A CTA bus passes by Rate Field. (Photo by Joseph Weiser/Icon Sportswire via Getty Images)

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]

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

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

Friday, May 30

😉 I’ll catch you out on the town this June. Don’t forget about those new speed cameras!

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