
City Cast Chicago
🤔 Is it still summertime Chi?
September 2, 2025 · — McKenna Harford
Good morning! City Cast editor McKenna Harford here to fill in for Emmi today 👋
Need some ideas on what to do this month? Check out our September guide for our tips on how to make the most of the last of summer! (Or is it the start of fall?)


What's CITY Talking About?
Portage Park Debuts Pedestrian Safety Measures
New speed bumps, curb extensions, and bike lanes were installed around the park itself and an elementary school to improve pedestrian safety and calm traffic. Long Avenue is one of the more dangerous neighborhood streets for traffic crashes. [Block Club]
- Related: Will the changes help the city reach its Vision Zero goals? [City Cast Chicago 🎧]
Advocate Health Cuts Youth Gender-Affirming Care
The hospital announced it would stop offering gender-affirming care, including hormone therapy, for patients under 19 out of fear of losing federal funding. Advocate is the sixth Chicago-area health provider to shut down gender-affirming care for youths. [Sun-Times]
Immigration Enforcement Surge Planned
ICE, Border Patrol, and other federal agencies are planning to send hundreds of officers to the city in an effort to increase arrests of undocumented immigrants. It’s unclear how long the arrest efforts will last. [NBC5 Chicago]

Your Guide to Chicago in September 2025

The end of summer can feel tragic in Chicago, but don’t worry — temperatures shouldn’t drop consistently till the end of the month. That means there are about 30 warm days left. Take advantage!
Jazz — And Other Fests
Stave off the end-of-summer blues with jazz. Options include:
- 🎵 Sept. 4, Sept. 11 | Record Row Concert Series | Willie Dixon’s Blues Heaven Foundation | South Loop
- 🎵 Sept. 8 | First Monday Jazz | The Arts Lawn | Washington Park
- 🎵 Sept. 18-20 | Englewood Jazz Festival | Hamilton Park Cultural Center
- 🎵 Sept. 26-28 | Hyde Park Jazz Festival | Various locations
Meanwhile, other fests continue all over the city. Art lovers, consider Renegade Craft Fair in Wicker Park, Lakeview East Festival of the Arts, and Ravenswood Artwalk.
And for the foodies: two Oktoberfests — one in Lincoln Square and one in Lakeview — Taste of Chicago in Grant Park, and Food Truck Festival in West Pullman.
Then, of course, there’s Riot Fest …
Riot Fest
After quite a fight, Riot Fest is back in Douglass Park this year Sept. 19-21. To strike a deal, Riot Fest pledged an additional $1 million to the park over the next five years.
This year’s headliners include Blink-182, Weezer, and Green Day. And — probably — John Stamos will perform. Fest founder “Riot Mike” just got a Stamos tattoo on his leg, which was one of the actor’s demands to drum for the Beach Boys’ set. Riot Fest has a longstanding meme-y obsession with the actor.
Mexican Independence Day
The 54th Annual Mexican Independence Day Parade will take place Sept. 14 along 26th Street, while the accompanying fest, El Grito Chicago, will occur in Grant Park Sept. 13-14.
This year’s theme is “Pride and Power: Our Strength, Our Legacy.”
Drivers — be ready for car caravans.
Chicagohenge
Chicagohenge is a twice-yearly phenomenon when the sun lines up perfectly with Chicago’s grid. This fall, it’ll happen Sept. 22-25. Head to the Loop to capture building-framed shots, but you should be able to see the burning orange golden hour from just about any east-west street.
Got other things you’re excited for in September? Hit us up at [email protected]!

What To Do
Tuesday, Sep. 2
- 🎤 Tuesday Funk | Hopleaf | Andersonville
- 🍽️ Maria’s Patio Jam | Maria’s Packaged Goods & Community Bar | Bridgeport
- ⚾️ Cubs vs. Braves | Wrigley Field
- 🍎 Lincoln Square Farmers Market | 4513 N Lincoln Avenue
- 🛍️ Low-Line Market | Southport Brown Line | Lakeview
- 🎲 The Twenty-Sided Tavern | Broadway Playhouse | Loop
- 🎶 93XRT Pop-Up Concert | Reggie's Rock Club | Prairie District
- 🎥 “Ratcatcher” | Gene Siskel Film Center | Loop
- 🎹 Christopher L. Wilson Trio | Colvin House | Rogers Park
- 🌳 Foraging Walk | LaBagh Woods | North Park
Have a great day!
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