CONTEST LAUNCH DATE:  Wednesday, May 13, 2020

ACCEPTING SUBMISSIONS UNTIL: Sunday, June 15, 2020 at 11:59pm

WINNERS ANNOUNCED: Sunday, June 22, 2020


Students who are eligible for the 2020 SSW Essay Contest are:

  • Currently in grades 6-12
  • Currently enrolled in a school located on the South Side OR currently live on the South Side


Please include the following information:

  • Name (and pronouns)
  • School Name & Grade
  • Address
  • Email 
  • Phone Number
  • Twitter/Social Media handles (if applicable)
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All essays should respond in some way to the essay contest theme:

“When You Say Chicago”

when i say Chicago
i mean the lake
(& i mean all of it).
i mean the candy lady at Rainbow
& the paleta man at Calumet
& the kids careening across the green at Montrose
& the jogger in midwinter daring a death for fitness.

when i say Chicago
i mean Cabrini & Stateway & Ickes & Ida.
i mean the city i’ll tell my kids in the past tense.
i mean the rents that sometimes
make me mean Georgia or Indiana or Dolton.

when i say Chicago
i mean my mama’s house
that was my grandma’s house.
i mean the neighborhood
that was our neighborhood
because fear left
& we said:
we’ll make a home here
& we’ll stay.

— excerpt from When I Say Chicago by Nate Marshall (Feb. 2017, Chicago Magazine)


What do you mean when you say Chicago?

We’re looking for pieces that delve into and explore how you find, define, build, and maintain a sense of community in Chicago. How do you feel connected to your neighbors? How do you feel connected to the city?

What people, places, or institutions in Chicago or your neighborhood act as community anchors? Tell us about them, how you’ve interacted with them, and what they’re doing right now to serve your neighborhood. How do they help you feel connected to your neighbors, even in times of crisis? What could city leaders and policymakers do to lift and support their work? Some examples of community anchors are: schools, local organizations and leaders, and historic landmarks.


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Please submit all submissions through the following Google form.

All submissions must be attached as a link to a Google Doc file with *edit access* or a Word document (.docx). Alternatively, submissions can be copied and pasted into the text box included on the form.

Essays should range from 500-1500 words and have a title. 

Three student essays will be chosen as winners to have their essays printed in the South Side Weekly, and will receive additional Weekly swag.

Questions? Please email