Best of the South Side (BoSS) is a year-round 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 year-round on a rolling basis, online and in the biweekly print edition of South Side Weekly, to make sure our readers don’t miss out on all the great things happening on the South Side. Once a year, we put together a special edition compiling all the bests from the previous year. 

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.
  • Show up to editor office hours: Want to run your idea by an editor first? Schedule a time to meet with a Weekly editor.
  • Attend an upcoming workshop: We’ll be partnering with community organizations around the South Side to host workshops that give participants an overview about the Weekly and Best of the South Side. This will be an opportunity to brainstorm initial ideas with the help of our team and learn about all of the other ways to get involved with the Weekly.

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.

How can I sign up to host a workshop for my community?

If you’d like to host a workshop with us, email our Program Manager

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