Andrew Wimer
Andrew Wimer · June 15, 2026

CHICAGO—The application period is now open for the 13th Annual South Side Pitch, the annual business pitch competition where entrepreneurs and small businesses compete for over $40,000 in prizes. Applicants can visit https://ij.org/ij-clinic-on-entrepreneurship/south-side-pitch/apply-to-south-side-pitch/ for contest details and to apply. Since its inception, the Institute for Justice Clinic on Entrepreneurship-hosted competition has been a powerful demonstration that the South Side is home to inspirational individuals determined to improve their lives and their community.

“We love to hear and share the stories of creative entrepreneurs, who are anchors in their neighborhoods,” said Beth Kregor, the director of the Institute for Justice Clinic on Entrepreneurship. “In our work, we see every day that small business owners are courageous and resilient as they take on many challenges. South Side Pitch shines a light on all they accomplish in and around the South Side.”

South Side Pitch lets promising entrepreneurs share their success stories and the impacts their businesses have in a “Shark Tank” style contest, with the final contestants presenting their pitches on Thursday, October 15.

South Side Pitch encourages entrepreneurs past the idea stage—established businesses with a track record of serving customers—to apply. In the semifinals, a group of applicants will be invited to submit a one-minute video to the South Side Pitch Chicago YouTube channel. Finalists from that pool will have the opportunity to present in person in October. The application period for South Side Pitch is now open and will close on Monday, August 3.

Prior winners have used their prizes to expand their businesses and create new jobs. Last year’s first-place winner, Runaway Cow, a vegan ice cream parlor, used its winnings to purchase new kitchen equipment, expand the parlor’s offerings and supply its delicious treats to restaurants across the Chicago area.

South Side Pitch is hosted by the Institute for Justice Clinic on Entrepreneurship. The contest is sponsored by the Coleman Foundation, the Polsky Center for Entrepreneurship and Innovation, and the University of Chicago Office of Civic Engagement. To learn more, visit www.southsidepitch.com. 

The Institute for Justice Clinic on Entrepreneurship provides free legal assistance, access to resources and advocacy for low-income Chicago entrepreneurs. To learn more about the IJ Clinic, visit www.ij.org/clinic.