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Neighborhood Guides

Your Guide to September 2026 in Chicago

Posted on September 1   |   Updated on September 4
Emily Mack

Emily Mack

Three excited men, The one in the left is in regular clothes and is smiling and clapping. The one in the middle is in a football jersey with a cheese grater hat. He is yelling and grating cheese. The one on the right is laughing and also wearing a cheese grater hat

Never forget that glorious comeback on Jan. 10, 2025. (Cooper Neill/Getty Images)

This summer's weather was a ripoff. (So were the vibes, if I’m being honest). So, let's 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.

City Cast

Your Guide to September 2026 in Chicago

00:00:00

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.

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:

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!

Team Tips and Picks

A woman in an orange dress holding a cup and a microphone. In the background it shows a screen from a side angle of this person

Chicago’s own Noname grew up in Bronzeville. (Scott Dudelson/Getty Images for Coachella)

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.

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.

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)

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