Advertisement image
CITY CASTChicago
Monthly Guide

Monthly Guide

😎 Make the most of August in the city

July 31, 2026 · — Emmi Mack

Hey Chicago! Another month, another monthly guide! Naturally, this one is jam-packed as Summertime Chi continues. We’ve made it through toxic air and terrifying storms … let’s enjoy this month to the fullest!

Your Guide to August 2026 in Chicago

Two students walking across the road. There's a cross guard in the background holding up a sign
Students on their way to Carl Von Linne Elementary in Avondale. (Talia Sprague/Chicago Tribune/Tribune News Service via Getty Images)

Kids may be starting school this month, but summer is still in full swing! Here are the stories and events we have our eye on.

Back to School

The Chicago Public School year starts Aug. 24. Here’s everything parents need to know, including that dreaded school supply list. Meanwhile, the school board just rejected CPS’ proposed budget, opting to approve a revised plan that avoids layoffs. Stay tuned for more on that.

  • Can I just say? School in August feels so wrong! When I attended CPS, we started the day after Labor Day.

Fun in the Sun

Throughout the summer, I’ve reminded you of Chicago’s many splashy water activities. Well, I’m gonna keep doing it! Just last week, I swam at Humboldt Beach for the first time, and it was lovely!

This month, there’s also the annual Chicago Air and Water Show. Before you freak out about the sonic booms — yes, literally — save the dates: Aug. 15 and 16.

Meanwhile, one of the city’s biggest traditions on land returns: the Bud Billiken Parade, now in its 97th year. Curious where the name comes from?

Final Summer Fests

If you haven’t hit a Chicago street fest this summer, now’s the time! Mark your calendars:

Extreme Weather

Whether August brings another official heat wave, time will tell. Regardless, it’s always pretty damn hot. Know your resources:

Team Tips and Picks

Two bowls of tomatoes in a garden
One day’s yield from my parents’ garden. (Emmi Mack / City Cast Chicago)

Every month, the City Cast Chicago team tells you what we’re eating, where we’re going, and anything else that sounds fun!

Emmi: Tomato Season (Almost) Upon Us

Soon, you may notice the slices on your hot dogs are less wimpy than usual. August, into September, is juicy tomato season in Chicago. I’m lucky — my dad turned his backyard into something of a tomato forest. But whether you’re buying, gifting, or receiving tomatoes, here are some ideas for the bounty.

Jacoby: Crosstown Classic

The Sox won their first series against the Cubs in May. Now, the matchup is headed north August 17-19. My last game inside Wrigley was for the classic five years ago. But now that both teams are playing meaningful baseball into August, I might suck it up and make the trip. The Sox lead their division, and the Cubs have an MVP candidate.

  • Biggest downside: The food at a Sox game is far superior.

Michelle: City Beach Bum

Peak swimming season is among us. Lake Michigan is its warmest in August, and so I’ll be taking advantage by getting my beach time in all month. There will be fewer kids crowding the beach as they return to school this month, so you might catch me on my laptop at 12th or 31st Street Beach during work hours.

Chima: Feeling Lolla-esque

I don’t have the mental fortitude for Lollapalooza, but I have a ton of talented friends who are participating in the festival weekend. Luckily for me, there’s no shortage of after-parties and performances, so I get to enjoy the fun while dodging the frenzy.

Tickets to Get Now (Before It’s Too Late)

Jump in the lake, eat a hot dog, wander in the sun … summer won’t last forever!

Free · Monthly Guide

More from Monthly Guide

Read latest