
City Cast Chicago
☕️ An artistitc walk through Woodlawn
June 29, 2026 · — Emmi Mack
Drumroll please! The winner of the 2026 Chicagoland’s Best Hot Dogs Tournament is … in Des Plaines! Rand’s Red Hots serves depression-style dogs à la Jimmy’s or Gene and Jude’s. And although it opened in 2012, it looks like a retro drive-in.
This has been your morning hot dog briefing.

What's CITY Talking About
Get Ready for the Heat Wave
Yeah, yeah, June was a mild start to summer. But now, Chicago is set to feel like 100 degrees all week, with actual highs in the 90s. [NBC 5]
- Hot and muggy: “Corn sweat” is back! [Block Club]
- Be prepared: Chicago has extreme heat resources. [City of Chicago]
Will CPS Lock In Budget Earlier This Year?
Chicago Public Schools leaders expect to approve a budget for the upcoming school year by the end of July. Facing a projected $700 million deficit, they hope to wrap up the budget early to secure a short-term loan needed to cover operating costs. [Tribune 🔒]
- Last year was … a struggle. [City Cast Chicago 🎧]
Are Chicago’s Parking Meters Cursed?
Chicago’s infamous parking meters are up for sale, and in a meeting last week, alders (finally) got more insight into the mayor’s rescinded bid to buy them back. Reps from prospective buyers also weighed in. All that and more on today’s podcast. [City Cast Chicago 🎧]
Orchards on the West Side
Ten vacant lots in Garfield Park, along West 5th Avenue between Sacramento and Kedzie, are turning into community orchards. In addition to providing fruit, they’ll help prevent flooding by increasing the tree canopy. Ground broke last week. [Block Club]
- Flooding woes: Infrastructure is outdated on the South and West Sides. [City Cast Chicago 💻]
Chicago’s Next LGBTQ+ Hub
In the last two decades, same-sex households more than doubled on the Southeast Side, including South Shore, South Chicago, East Side, Hegewisch, and South Deering. Residents cite lower costs of living compared to North Side “gayborhoods” and changing attitudes in areas that were more conservative. [Sun-Times]
- Growing, but not new: The South Side has long been home to LGBTQ+ businesses like Club Escape on 75th Street. [Block Club]

What To Do
Monday, June 29
- ⚾ Cubs vs. Padres | Wrigley Field
- 🌝 Full Moon Jam | Foster Beach | Uptown | Free
- 🎶 Free Summer Music Series | MIllennium Park | Loop
- 🤘 Punk Rock Monday | Delilah’s | Lincoln Park | Free
- 🕺🏻 Curls Ultra album release | Empty Bottle | Ukrainian Village | Free
- 🏳️🌈 {THE} HOUR | The Den Theatre | Wicker Park
- 👩🏻🔬 Science Social | Half Sour | Loop
Tuesday, June 30
- 🎨 The Portal | Experimental Station | Woodlawn | Free
- 🎥 “Independence Day” | Millennium Park | Loop | Free
- 🎤 Big Cheese Poetry Slam | Zhou B Art Center | Bridgeport
- ⚾️ Cubs vs. Padres | Wrigley Field
- 🏳️🌈 Pride Book Celebration | Uptown Branch | Free
- 🪄 MAGIC IS REAL | Logan Arcade | Free
- 🎭 “The Importance of Being Earnest” opens | Oak Park Festival Theatre
- 🖼️ Tuesdays at the Terrace | Museum of Contemporary Art Chicago | Streeterville | Free
- 🐟 Free night | Shedd Aquarium | South Loop
In honor of Woodlawn, I leave you with some Minnie Riperton 💕💕
Free · Daily



