Since 2012, South Side Weekly has produced our Best of the South Side (BoSS) issue to showcase people, places, events and businesses on Chicago’s South Side, with all content produced by South Siders. 

Our Focus

BoSS provides a platform for community members to capture why the South Side is special, and who and what makes it so. It’s also a space to reflect on the history of the South Side, and engage how this dynamic, vital region in the city continues to evolve.

This year, we’re prioritizing selections from the following neighborhoods:

Video shot and edited by Isabel Nieves

Get Involved

• Guidelines: Read our guidelines below on what makes a good “Best” in the Weekly and look over our issues from previous years to see what’s already been covered and how.
  
• Submit: Ready to submit an idea for something you’d like to write about? Fill out this BoSS submission form if you’re new to the Weekly or this form if you’re an existing contributor and an editor will follow up with you in 1-2 weeks. The deadline to fill out this form this year is Friday, July 10, 2026.
  
  Filling out the BoSS submission form is the first step. We’ll have virtual orientations in early July, and ask South Side writers to submit expanded pitches for Bests by July 24. Weekly editors will review the submissions to see if they’re a good fit and get back to you within one week. If accepted, you’ll be paired with an editor and write your Best in August, submitting by September 4, 2026.

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2026 Timeline

Here’s the timeline and key dates:

First two weeks in July (details coming soon!): Virtual BoSS orientation
July 17: Deadline to submit the BoSS form
July 24: Deadline to submit expanded Best pitches
Early August: Decisions reached and accepted writers paired with editors
August 24: Deadline to send first drafts of Bests
Late August/Early September: Edits and fact-checking
September: Best of the South Side 2026 is published!

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Best Entries

What makes a good Best story?

People have written about everything from art pop-ups, to bait shops, to local street vendors. We’d like the Best features to run between 800-1000 words this year, and incorporate some history about the profiled person/place/event. Sharing some examples of Bests, from years past:

The 2026 Best of the South Side will include these categories:

• Community Organizing: tenant unions, block clubs, immigrant rights organizations
• Third Spaces: barbershops, parties, bowling alleys
• History: places of historical interest, organizations dedicated to history and memory
• Food & Drink: restaurants, bars, coffeeshops, grocery stores, you name it
• The Great Outdoors: parks, nature areas, and other public spaces
• Learning & Education: dance classes, hobby clubs, library programs, museums
• Culture: traditional events, art galleries, music venues

If you’re not sure if your idea fits any of these categories, submit it anyway! 

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Browse the Archive

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