Monthly Guide
☀️ September is still summer
September 1, 2026 · — Emmi Mack
Rip off! That’s what Chicagoans are saying about this summer’s weather (and vibes, if I’m being honest). So, I will not take September sitting down. Summertime Chi WILL continue for one more month, I’m officially announcing right now. This guide will not include pumpkin spice. It will not include light jacket reminders. Instead, here’s how to make the ABSOLUTE most of September.
Your Guide to September 2026 in Chicago
Football Season Begins
Lately, most Chicago Bears talk has hinged on the team’s stadium standoff. (Here’s where we’re at with that, by the way.) But now it’s time to pivot to actual football. Last season was enough to turn even the grouchiest sports-haters — myself included — into megafans. Will they keep making fourth-quarter history? The road starts Sept. 13.
- Before Hammond: Enjoy a game at Soldier Field.
Theater Season Abounds
September marks fall theater season here in Chicago. For musical fans, there’s “Dirty Dancing” and “Jekyll & Hyde.” At smaller spaces, consider “Black Girl From a White Suburb” at American Blues Theater and “How We Got On,” about 1980s teens and hip-hop, at Definition Theatre.
- Personally: I’m looking forward to “The Attic” at the Goodman Theatre, based on the memoirs of a trapeze artist, and “Kowalski” at Lookingglass Theatre, which follows Tennessee Williams and Marlon Brando.
Latino Heritage Month
Another theater gem this month: The 9th annual Chicago International Latino Theater Festival kicks off Sept. 17. Latino Heritage Month runs through mid-October, making it the perfect time to support local Latino businesses. More official ways to celebrate include:
- 🎶 18th Annual ¡Viva La Hispanidad! | IO Godfrey | Loop | Sept. 11
- ⚾️ The Cubs’ Hispanic and Latino Heritage Month Celebration | Wrigley Field | Sept. 15
- 👠 Salud’s Gala | National Mexican Museum of Art | Pilsen | Sept. 16
- 💀 “Where Memory Lives: 40 Years of Día de Muertos” opening | National Mexican Museum of Art | Pilsen | Sept. 25
Riot Fest — and Other Fests
Riot Fest returns to Douglass Park the weekend of Sept. 18, and this year William Shatner is a special guest. Headliners include Twenty One Pilots, Iggy Pop, Tool, Pierce the Veil, Elvis Costello, and (my idol) Alanis Morissette. Meanwhile, many — many! — Chicago street fests continue!
In the News
All month long, we’ll continue covering Chicago’s ongoing budget back-and-forth. The mayor must submit his own proposal by Oct. 5. Here at City Cast, we’re also gearing up for the general election on Nov. 3. (Remember? Here’s who’s on the ballot.) Stay tuned!
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Team Tips and Picks
Every month, the City Cast Chicago team tells you what we’re eating, where we’re shopping, and what else we’re planning for.
Jacoby: Two Can’t-Miss Concerts
This month, I am seeing two of my favorite artists on back-to-back nights. I’m starting with Jungle at the United Center Sept. 10, followed by Noname at Park West Sept. 11.
- Listen: Noname is on our ultimate Chicago hip-hop playlist.
Emmi: MORE BEACH!!!
Public pools close the day after Labor Day, and fall technically starts Sept. 22. But as stated above, I’m pretending September is still true summer. Catch me tanning at the Montrose ledge month-long, hitting seasonal hot dog carts, and going hard on Labor Day.
- Remember: The water should still be warm.
- On another note: I’m visiting Lithuania for the first time this month! But I’m a bad Lithuanian. I know nothing about my heritage. So, I’m excited to hit the Balzakaz Museum in West Lawn before I go 🇱🇹
Michelle: Plants and Poetry
I’m checking out Plantasia, a two-day celebration of ambient and electronic music throughout the Garfield Park Conservatory’s nature campus. I’m also looking forward to reading at Palabra Pura, an open mic by the Guild Literary Complex in collaboration with Brighton Park Poets. Palabra Pura is a bilingual reading series that showcases the work of Latino writers in Chicago.
Simone: Housewarming
I’m finally moved into my new place, and now it’s time to party! I’m making good use of one of our old neighborhood guides, and will endeavor to build a nice charcuterie plate from Gene’s Sausage Shop. Also, if anyone has a line on where to find inexpensive large rugs, let me know!
Tickets to Get Now (Before It’s Too Late)
- Sept. 3-6: Sound and Gravity Festival | Multiple Locations
- Sept. 4-6: ARC Music Festival | Union Park | Near West Side
- Sept. 4-6: North Coast Music Festival | SeatGeek Stadium | Bridgeview
- Sept. 7: Danny Elfman | Aragon Ballroom | Uptown
- Sept. 7: Fire vs. Miami | Soldier Field | South Loop
- Sept. 10-11: Plantasia | Garfield Park Conservatory
- Sept. 10: Jungle | United Center | Near West Side
- Sept. 12-13: El Grito Chicago | Grant Park | Loop
- Sept. 12-13: Evanston Folk Festival | Lakefront at Dawes Park
- Sept. 13: Both Sides of the Street | Ramova Loft | Bridgeport
- Sept. 14: The Moth: Nine to Five | The Den Theatre | Wicker Park
- Sept. 14: Bikini Kill | Salt Shed | Goose Island
- Sept. 18: Story Fest | Athenaeum Theatre | Lakeview
- Sept. 18-19: Phoebe Bridgers | The United Center | Near West Side
- Sept. 18-20: Riot Fest | Douglass Park
- Sept. 26: M.E.H | Dorian’s | Wicker Park
- Sept. 29: Mon Rovîa | Salt Shed | Goose Island
Now get outside! I recently hit the Sea Dog Extreme, and even the gloomy sky couldn't dampen the thrills. (Extreme rides end Sept. 7, but the classic Sea Dog runs through early November.)
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