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Your Guide to August in Chicago

Posted on August 1, 2024   |   Updated on September 30, 2025
Sidney Madden

Sidney Madden

Lollapalooza at Grant Park in 2021

Lollapalooza at Grant Park in 2021. (Scott Legato / Getty)

City Cast

Your Guide to August in Chicago

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Don’t let August slip away into a moment in time — enjoy the last of summer and prep for the new school year.

Lollapalooza is Here

Hundreds of thousands of festivalgoers will be at Grant Park to see big acts like SZA, Chappell Roan, and the Killers this weekend. If you’re going, take care of yourself and others. That could mean keeping an eye on the weather or learning to administer an overdose reversal drug.

Keep the party going at official aftershows.

City Cast

New CTA Stop, Heat and Storms Return, and Gator Watch?

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The DNC security perimeter around the United Center

The DNC security perimeter around the United Center. (City of Chicago)

Brace Yourself for the DNC

Prepare yourself for traffic and protests: The Democratic National Convention is taking over the United Center, McCormick Place, and surrounding areas leading up to and during the event Aug. 19–22.

That’s also when your favorite restaurants near the venues are expecting to see fewer regulars — consider supporting them more this month.

Pregame the DNC at the Illinois State Fair the week before or at Lisa Beasley’s “Unpolitical Women” show Aug. 18, aka DNC Eve.

City Cast

Butter Cows, Kissing Babies, and Piglet Parades: The Illinois State Fair is Back

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Soak Up the Summer

Cue the sad music: Some Summertime Chi programming is coming to an end 🎻 Free workouts and movies in Millennium Park are wrapping up this month. The Museum of Contemporary Art’s Tuesdays on the Terrace series is also ending.

It’s Time to Go Back to School

City Cast

Will Chicago See Another Showdown Between School District and Teachers?

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What can families do to prepare? Get school supplies — check out giveaways including the Bud Billiken Parade. Request plant-based lunch for your vegan student. Ride the CTA on the first day of school — it’s free!

City Cast

Why Is Largest Black Parade Called the Bud Billiken?

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We didn’t forget about educators: The Creative Chicago Reuse Exchange in Auburn Gresham has a teacher supply giveaway Aug. 23–25.

Can You Squeeze in One Last Getaway?

Trying to leave town during the Air and Water Show? The DNC? Just before the school year starts? Stay tuned for an upcoming City Cast Chicago episode with with American Weekender editor Amy Cavanaugh who recommends spots to eat in places like Milwaukee and Cleveland.

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