City Cast Chicago logo

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

00:00:00

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?

00:00:00
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

00:00:00

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?

00:00:00

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?

00:00:00

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.

Share article

Hey Chicago

Stay connected to City Cast Chicago and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

The latest in Chicago

Chicago, ExplainedAugust 21

Take This Week's Chicago News Trivia Quiz

How closely were you paying attention to this week's current events in Chicago? Test yourself in our weekly trivia quiz.

A man in a cubs uniform bracing for a man in a white sox stealing a base
Keep It LocalAugust 20

How Transit Tees Turns Chicago’s Quirks Into Board Games

From board games about the city’s history to puzzles of iconic maps to card decks featuring local wildlife, Transit Tees’ teams of creato...

A person writing on a gridded paper that says "Chicago 1893" There's also a board game with an assortment of different houses for the board game on it. There is also A bowl of popcorn and a soda on the table
Keep It LocalAugust 20

Your Guide to Chicago’s Toy Stores

From vintage toys to a workshop series for aspiring toy inventors, Here's a list of places that’ll help you spoil the kids in your life a...

A table with an assortment of different stuffed animals
Keep It LocalAugust 13

Your Guide to Chicago’s Stationery Stores

Whether you’re actually going back to school soon or you just love analog hobbies, these local shops will help you find all kinds of stat...

A large group of people inside a store. They are looking at an assortment of items
Food & DrinkAugust 13

5 New Spots to Dine and Drink

Chicago is hot AF right now — and so is the dining scene. These recent openings have caught our eye.

A room with velvet drapes on every wall. On the ceiling there are chandeliers and people are sitting at a booth
Keep It LocalAugust 13

Family-Run Atlas Stationers Has Supplied Chicago’s Pens For Decades

For decades, the family-run shop delivered office supplies in bulk to offices in the Loop.

The outside of a brick building, the sign says "Atlas Stationers Inc"
Keep It LocalAugust 6

Your Guide to Dog-Friendly Patios

Want to enjoy patio weather, but hate leaving your pup at home? Check out our guide on the best dog-friendly patios in Chicago.

A curly-haired golden doodle wearing a harness steps into a small blue kiddie pool filled with colorful beach balls at a dog-friendly outdoor patio, with diners seated under blue and white striped umbrellas in the background.
Keep It LocalJuly 30

Why Creatives Love Epiphany Center for the Arts

Five years ago, a group of artists transformed a shuttered, historic church at 201 S. Ashland Ave. into Epiphany Center for the Arts. Sin...

An indoor space with hanging lights and a wood floor. The walls are short but the roof is very tall. There are small remnants of a church left like the windows