City Cast Chicago
🍧 Italian ice is back in Chicago
May 1, 2025 · — Emmi Mack
Happy May! Spring is in full swing, and we’re in the final 48 hours of our spring membership campaign. If you haven’t joined yet, there’s still time!
Let me be straight up: We send this newsletter out to thousands of Chicagoans every day, totally free. We don’t paywall our content because we believe in accessible journalism that informs, connects, and strengthens our city. But we need Neighbor support to keep it that way.
When you join, you get all the new perks of our expanded membership program, like the chance to shout out a local business or nonprofit. Read on for the first round of Neighbor shoutouts.
What Chicago's Talking About
Today, a May Day Rally Against Trump
Chicago’s May Day rally begins at Union Park at 11 a.m. From there, the crowd will march to Grant Park for speeches from labor and immigration advocates. The event comes two days after President Donald Trump signed executive orders targeting sanctuary cities like Chicago. [WTTW]
- Related: Here’s why ICE is being sued. [City Cast Chicago 🎧]
Johnson Pushes for Funding in Springfield
Mayor Brandon Johnson appeared in Springfield Wednesday as Chicago faces a looming budget gap. Johnson is asking for increased investment in the joint city-state shelter system for migrants and homeless people and more money for Chicago Public Schools. [Tribune 🔒]
Neighbors Protest Luxury Hotel in Woodlawn
Residents of South Shore and Woodlawn are protesting a proposed hotel near the Obama Presidential Center. The hotel would be a luxury project, rising 26 stories tall on Stony Island Avenue next to an affordable housing development. Neighbors are worried about how the Obama Presidential Center has already raised rents in the area. [Sun-Times]
Neighborhood Shoutouts
Introducing Neighbor shoutouts! We’ll hear from a few City Cast Chicago Neighbors each week about their fave local people and spots.
- Nicole R. of South Shore is shouting out Greater Baking on 71st Street, which does cupcakes, ice cream and now, breakfast: “I'm so excited for the pistachio iced matcha!”
- Sean M. of Avondale is shouting out the Avondale Gardening Alliance: “They are one of the most effective groups in the neighborhood for bringing neighbors together to connect and build community.”
- Lee W. of Albany Park is shouting out Tailwinds Cycles on Lawrence Avenue: “Steven and his team are always going above and beyond to keep my bike in top shape and also recently donated two bike tuneups for a raffle fundraiser I'm helping organize.”
Become a City Cast Chicago Neighbor to share your own shoutout in this very newsletter — and on the podcast!
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What To Do
Thursday, May 1
- 🪦 May Day Outdoor Exhibit | 9 a.m. to 4 p.m. | Free | Forest Park
- 📚 Story Time | 9:30 a.m. | Free | Lincoln Square
- 🚶🏽♂️ May Day March | 11 a.m. | Free | Union Park
- 💪 CEO Roundtable: Latinas Poderosas | 5 p.m. | Free | Loop
- 🍾 Portuguese Wine Exploration 6-8 p.m. | $50 | West Town
- 🍷 Spring Wine Stroll | 6-9 p.m. | $60 | Lincoln Square
- 🎼 Hope & Art | 6-8 p.m. | Free | Lyric Opera
- 🃏 Indie Board Game Showcase | 6 to 10 p.m. | $15+ | Wicker Park
- 🎭 “Berlin” | 7:30 p.m. | $24+ | Hyde Park
- 🎻 Mariachi Fuego | 7:30-9 p.m. | Free | UIC Recital Hall
- 🎷 Matthew Whitaker Trio | 8-9:30 p.m. | $30+ | South Loop
- 🎭 “Spring Awakenings” | 8 p.m. | $15 | Lincoln Park
- ✨ Twilight Fest | 8 p.m. to Midnight | $20+ | Near South Side
Friday, May 2
- 🍝 First Fridays at Eataly | 3-7 p.m. | $25 | Streeterville
- 👮🏻♂️ Chicago Leather Pride | 3 p.m. to 4 a.m. | Varies | Edgewater
- 👀 Open Studios at Hubbard Street Lofts | 6-10 p.m. | Free | West Town
- 🎉 AACM 60th Anniversary Concert | 7-9 p.m. | $7-32 | Woodlawn
- 🎼 Scott Joplin’s “Treemonisha” | 7:30 p.m. | $39+ | Loop
- 🍺 ”Drink the Past Dry” | 7:30 p.m. | Suggested Donation | North Center
- 🎭 “Spring Awakenings” | 8 p.m. | $15 | Lincoln Park
- 🍾 Rooftop Party: Lit Fridays | 8 p.m. to Midnight | $20+ | Chinatown
- 🖤 Emo Night | 9 p.m. | $21 | Wicker Park
- 💥 Free Comic Book Day Pre-Party | 9 p.m. | Free | Wrigleyville
- 🎵 Afro Fusion Friday | 11 p.m. to 4 a.m. | Free-$50 | Uptown
We need your support during this membership campaign. We need it like you need this City Cast Chicago Neighbors mug.
And on that note, a big thank you to these future mug owners, our newest City Cast Chicago Neighbors: Nichol R., Scott M., Robert D., Laurie M., Brandy V., Nicole R., and Stephen E.
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