Best of the South Side (BoSS) is a showcase of the people, places, events, businesses, and oddities on Chicago’s South Side, written by South Siders.
BoSS is an opportunity for community members from all over the South Side to capture who and what makes the South Side special for them. Our “Bests” are published in a special edition of the paper each September.
The video below from 2022’s ten-year anniversary of Best of the South Side captures how this effort empowers community members to own the stories of their neighborhoods.
Video shot and edited by Isabel Nieves
Get Involved
- Submit your Best: Ready to submit an idea for something you’d like to write about? Fill out the BoSS submission form and an editor will follow up with you in 1-2 weeks.
Frequently Asked Questions
What makes a good Best?
Over the years, people have written about everything from art pop-ups, to bait shops, to local street vendors. This year we want Bests to come in at around 600-800 words in order to paint a thorough and colorful portrait of the subject. Here are a few examples of Bests that stand out from years past:






In these examples, we especially love:
- A clever title, such as “Best Place to Find Nemo”
- A community pillar, like “Best Movie Theater,” which for Chatham and the 87th Street Plaza has been a longstanding entertainment center for decades
- A community tradition, like “Best Healing Space,” where folks come together in an intimate setting to tend to themselves and each other
But these are just a few examples, and there is no limit to the number of rich stories that can lead to great Bests!
What’s the process look like for writing a Best?
After you submit your pitch through the BoSS submission form, a Weekly editor will review your suggestion to determine if it’s a good fit. You can expect to hear back within 1-2 weeks with a decision. If your first pitch is rejected for some reason, you will be encouraged to resubmit and/or attend a workshop or editor office hours. If your pitch is accepted, you’ll be paired with an editor to help guide you through the writing and reporting stage.
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