This summer and fall, small businesses from all around the South Side will compete to see who has the best story, the most meaningful impact, and the most exciting ideas for the future. The community and experts will join together to pick their favorites and decide who will win the grand prize. 

If you are a South Side small business owner, we would love to have you participate in the pitch. If you have a favorite South Side business, please let them know about the competition. And, if you’re a Chicagoan, even if you’re not competing, we hope you tune in and listen to the stories of these incredible entrepreneurs.  

South Side Pitch is hosted by the Institute for Justice Clinic on Entrepreneurship. Please stay connected by following us on our Facebook and Twitter

Event Details:

South Side Pitch 2021
Thursday, October 21, 5:30PM – 8:00PM
Polsky Exchange North (In-Person and Virtual Event)
1452 E. 53rd St., 2nd Floor, Chicago, IL 60615

Last Year’s Judges: Peggy A. Davis, VP of Community Impact, Chicago Community Trust || Vincent Williams, President and CEO, Chicago Minority Supplier Development Council || Susana L. Vasquez, Associate Vice President, The University of Chicago Office of Civic Engagement|| Elizabeth Kregor, Director, IJ Clinic on Entrepreneurship

Last Year’s Finalists:

Children’s shop focused on representation and inclusivity.

Maestri Tutoring
Bilingual tutoring center for working class families.

New Magnolia Garden Center
A U-pick farm and garden center located in Back of the Yards.
A marketplace of Black-owned businesses that includes an online business directory and a brick and mortar shop in Chatham.

The Lemonade Land
Pop-up market for micro Black-owned businesses in the South Shore, Greater Grand Crossing, and Woodlawn area.

Wesley’s Shoes
Sit and fit family shoe store serving customers since 1970.


Members of the media: if you are interested in hearing more about South Side Pitch, please contact Erik Castelan at

How do I apply to be a contestant?
To apply please go to or click on this link. Deadline to apply is Monday, August 9 

Questions? Email or call 773-834-3129