
City Cast Chicago
🤔 So, what’s happening with the Red Line extension?
October 7, 2025 · — Emmi Mack
Did ya notice? The Kennedy Expressway is back to normal — or at least as normal as the Kennedy gets. After three years of construction, all four lanes are open. It’s a bright spot as Chicago grapples with more serious news 👇

What's CITY Talking About?

Chicago's Trump Lawsuit, Texas Troops, and ICE-Free Zones
Since Gov. JB Pritzker confirmed that President Donald Trump is federalizing Illinois National Guard Troops, updates are developing quickly.
- The city of Chicago and the state of Illinois sued the Trump administration to prevent National Guard deployment. A federal judge declined to immediately block troops but set a hearing for Thursday. [Tribune 🔒]
- Now, National Guard troops from Texas are already on their way to Illinois. Deployment could occur today or tomorrow. [CBS]
- Mayor Brandon Johnson has signed an order blocking immigration agents from using city-owned spaces. [NBC 5]

The Future Of The Red Line Expansion
The Trump administration is withholding $2.1 billion in federal funds for Chicago transit projects, including the long-awaited Red Line extension. On today’s episode, TaNesheha Marshall of the CTA and Andrea Reed with the Greater Roseland Chamber of Commerce recall why Far South Siders pushed for the extension. [City Cast Chicago 🎧]
ChiArts in CPS Limbo
ChiArts, Chicago’s only public high school for the arts, will not renew its contract with Chicago Public Schools amid financial strain. The current contract expires in 2026. As of now, the future of the school is unclear. [Block Club]
Sculpture Trail Unveiled on Northwest Side
Northwest Art Trail now officially connects Jefferson Park and Portage Park, along the 4000 and 5000 blocks of Milwaukee Avenue. The state-funded path includes five new sculptures plus five older sculptures, and murals. [Sun-Times]
- Have you passed by? Send pics to [email protected].
Sponsored Content

Step Inside Chicago’s Architectural Treasures in October
Open House Chicago, from the Chicago Architecture Center, returns October 18–19. Go behind the scenes at historic theaters, sacred spaces, skyscrapers, and neighborhood gems, 200+ sites across 25+ neighborhoods. Free and open to the public. Plan your weekend at openhousechicago.org

Fall Fests Coming Up in Chicagoland

As the feds descend on our city, it’s hard to think of much else. But Chicago is still Chicago. And Chicago is great in the fall.
There are so many ways to soak up autumn — carving pumpkins, watching scary movies, drinking Oktoberfest ales, dressing up for Halloween … Luckily, Chicago covers it all with festivals, parades, and pumpkin patches. Whether your ideal fall day is cozy, spooky, or crafty, we’ve got a recommendation for you!
Fall Fests
- 🚜 Fall Fest on the Riverwalk | Oct. 4, 11, 18, 25 | Riverwalk
- Take a hayride along the river and enjoy apple cider donuts at Island Party Hut’s autumn Saturday celebrations.
- 🧑🌾 Scarecrow Weekend | Oct. 10-12 | Downtown St. Charles
- Celebrate the 40th anniversary of Scarecrow Weekend this year by voting on your favorite handmade straw watchman or making a scarecrow-to-go.
- 🌾 Fall Festival at NPV | Oct. 19 | North Park Village Nature Center
- Newsletter Editor Emmi highly recommends putting your scarecrow-making skills to the test here. Afterwards, neighborhood lawns are populated with kooky creations.
- 🦁 Lincoln Park Zoo Fall Fest | Through Oct. 26 | Lincoln Park Zoo
- Enjoy a stroll through decorated gardens and watch the animals participate in the fall fun with themed enrichment toys!
- 🍁 West Chicago Fall Festival and Pumpkin Patch | Through Oct. 30 | Sonny Acres Farm
- Whether you want your hayride haunted or picturesque, this festival has options!

Pumpkin Paloozas
- 👻 Jack's Pumpkin Pop-Up | Through Nov. 2 | Goose Island
- Come for Chicago’s largest corn maze, stay to enjoy the food trucks and specialty cocktails.
- 🎃 Night of 1,000 Jack-o'-Lanterns | Oct. 8-12, 15-19, 22-26 | Chicago Botanic Gardens
- Get inspired by hundreds of artist-carved gourds featuring tributes to Chicago sports teams, landmarks, and legends.
- 🚜 Pumpkin Fest | Oct. 11-12, 18-19, 25-26 | Johnson’s Farm, Hobart, IN
- Pick your own pumpkins and squash — to eat or decorate with!

What To Do
Tuesday, Oct. 7
- 💡 Hydrosonic Light Show: Worldview Whirlwind | Wild Mile | Goose Island
- 🎻 Old Town School of Folk Music Happy Hour | Gallagher Way | Wrigleyville
- 🧘🏻 Morning Yoga | Gallgher Way | Wrigleyville
- 🎃 DIY Halloween Decor | Uni Uni Bubble Tea | Wicker Park
- 📖 "Don't Go: Stories of Segregation and How to Disrupt It" | Chicago Cultural Center | Loop
- 🤣 The Punch Up | Lincoln Lodge | Logan Square
Wednesday, Oct. 8
- 🎻 Mumford and Sons | United Center | Near West Side
- 🕺🏻 Pisco Disco | Tanta Cocina Peruana | Streeterville
- 👩🎨 Joan Jonas | Art Institute of Chicago | Loop
- 📖 "For the Sun After Long Nights: The Story of Iran’s Women-Led Uprising" | Women & Children First | Andersonville
- ⚾ Cubs vs. Brewers | Wrigley Field
- 🎃 Night Of 1,000 Jack-o'-lanterns | Chicago Botanic Garden | Glencoe
- 🎤 Comedy open mic | Cole’s | Logan Square
🍂 Once again readers, thanks so much for your continued support throughout our fall membership campaign. We did reach our goal!

Some City Cast Chicago Neighbors joined us over the weekend for birding at the Field Museum. It was a chirping good time! If you want to be in on the next hang, become a member … it’s not too late!
Free · Daily

