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Your Guide to Chicago in September 2025

Posted on September 2, 2025   |   Updated on September 30, 2025
Emily Mack

Emily Mack

The sun shines in the center of two downtown buildings.

Chicagohenge during this spring’s equinox. This fall, it’s Sept. 22-25. (Scott Olson/Getty Images)

City Cast

Your Guide to September 2025 in Chicago

00:00:00

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. You can kick things off Sept. 1 at the 8th Annual Labor Day Jazz Festival for $25. Later in the month, free options include:

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 LakeviewTaste 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.

Football Season

Da Bears season kicks off Sept. 8 at Soldier Field against the Minnesota Vikings. Will you be tailgating? This year could be one of the last to darty outside the ol’ Spaceship stadium. As of now, building a new Bears stadium in Arlington Heights is “the plan.”

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.

The Emmys

The last couple Emmy Awards were a source of hometown pride as “The Bear” swept. This year, TV’s biggest night takes place Sept. 14, and “The Bear” is nominated in most comedy categories, including Outstanding Comedy Series.

Personally, I am over “The Bear” … but I still love seeing Chicago repped at awards shows.

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 chicago@citycast.fm!

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