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
- 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 Monday, June 9!
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
What could I write about?
Every year we have Bests about restaurants, parks, and community organizations. But we also like to include Bests that focus on the history of a place or highlight ‘third spaces’ where people can connect outside of work, school, or home. Think outside the box and steer away from covering chain businesses unless there’s a personal or unique angle.
Here is the list of categories in this year’s BoSS with some examples of each one:
- Community Organizing: tenant unions, block clubs, immigrant rights organizations
- Third Spaces: barbershops, parties, bowling alleys
- Food & Drink: restaurants, bars, coffeeshops, grocery stores, you name it
- History: places of historical interest, organizations dedicated to history and memory
- 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!
Which neighborhoods can I write about?
The Weekly considers everything south of Roosevelt Road and within Chicago city limits to be the South Side. While we’ll be publishing writers and Bests from all over the South Side, this year we’d like more writers and entries from the following neighborhoods:
- Little Village & North Lawndale
- Pullman
- Back of the Yards
- Englewood & West Englewood
- Auburn Gresham
- Ashburn
- Hegewisch & East Side
What’s the process look like for writing a Best?
Filling out the BoSS submission form for new or existing contributors is the first step. We’ll have an in-person orientation and social in mid-June and ask South Side writers to submit expanded pitches for Bests by the end of June. Weekly editors will review the submissions to see if they’re a good fit and get back to you within 1-2 weeks. If accepted, you’ll be paired with an editor and write your Best in July and August.
Here’s the timeline and key dates:
June 9: Deadline to submit the BoSS form
June 12 or 13: BoSS orientation and in-person social (exact time and place TBD)
June 30: Deadline to submit expanded Best pitches
Mid-July: Decisions reached and accepted writers paired with editors
August 14: Deadline to send first drafts of Bests
Mid-August: Edits and fact-checking
September: Best of the South Side is published!
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