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 their neighborhoods in their own image, and to highlight their favorite aspects of their communities. 

After ten years, we’re reimagining BoSS: Going forward, our “Bests” will be 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. Then, once a year, we’ll put together a special edition compiling all the bests from the previous year. 

The video below from last year’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 in your neighborhood? 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: This year 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. If you want to bring Best of the South Side to your community organization or group, email our Publisher at!

Here are some of the BoSS entries that have been written so far!

Browse the Archive