Hey Chicago Southsiders,
It’s Back-to-School season!
There’s some good news for students who rely on public transportation. K-12 students can ride CTA, Metra and Pace for free on Monday, August 24, the first day of school. Read more here.
And while everybody is focused on getting through this school year, I also want to put something else on your radar.
If you have a middle school or high school student, this is actually one of the best times to start thinking about college costs. You do not want to wait until senior year and suddenly find yourself trying to figure out scholarships, financial aid and how you’re going to cover a huge tuition bill.
That’s a big reason why I wrote Debt Free Before Graduation. I wanted students and parents to know that there are things you can do before college to put yourself in a better financial position and potentially avoid taking on a mountain of student loan debt.
The earlier you start planning, the more options you have. So if college is somewhere on the horizon for your family, even if it still feels a few years away, now is a great time to start getting ahead of the game. Grab your copy here.
Homeowners also have an important deadline coming up. The second installment of 2025 Cook County property tax bills is due October 1, 2026. Physical bills are expected to be mailed beginning September 1, but you don’t have to wait for yours to arrive. Bills are already available online through the Cook County Treasurer’s Office, where property owners can view, download or pay their bill. Read more here.
And with school starting back up, there are also several back-to-school events, community gatherings and family activities happening across the South Side. We’ve rounded up a few to keep on your radar, along with other upcoming events as we head toward Labor Day weekend and September.
Keep scrolling for what you need to know and what’s happening across the South Side.
Help us tell the South Side’s story by joining Inside Chicago Southsider. Let’s make sure our contributions aren’t erased, overlooked, or forgotten—and show the world that ain’t no side like the South Side.
Let’s get into this weekend’s events!
Talk soon,
Charlene Rhinehart
Publisher, Chicago Southsider
Our August Event Guide is live, and it’s packed with ways to celebrate, connect, and explore all month long!
Check out a few events coming up:
The Sweet Mix DJs – Strugglebeard Bakery
Back to School Health Fair
Righteous Rise Back to School & Resource Block Party
Villapalooza Little Village Music Festival
National Park Week August 22-30
Hyde Park Farmers Market
Visit our August Event Guide here. Would you like to advertise in our event guide? Contact us at hello@chicagosouthsider.com.
Your August Guide to Local Fun & Festivals: From parades to historic festivals, check out what’s going on around Chicago this weekend!
August is National Black Business Month - Early Walker’s No Business Left Behind Initiative Launched This Summer: Through his new No Business Left Behind initiative, the Chicago entrepreneur is helping struggling small businesses access mentorship, capital, and operational support before they’re forced to close their doors.
South Side Pitch Competition: The next South Side Pitch Competition will take place in October. Learn more about last year’s pitch competition here.
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Visit ChicagoSouthsider.com for more content.
Warm regards,
Chicago Southsider
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