September 10, 2026

Public Invited to Select Their Favorite Neighborhood Businesses to Compete in Annual South Side Pitch

Group celebrates with award certificates at South Side Pitch 2025, as Sam Thousand plays trumpet
Sam Thousand (with trumpet) and other participants were in high spirits as Chicago small businesses competed in South Side Pitch 2025 for thousands of dollars in prize money.

CHICAGO—Public input determines one of the lucky finalists for this year’s South Side Pitch. For the 13th year in a row, South Side entrepreneurs will have the opportunity to win money, earn acclaim, and get training to fuel their business dreams through the South Side Pitch. The competition will again be held live and open to the public at the Polsky Center for Entrepreneurship and Innovation in Hyde Park. Through Monday, September 21, members of the public are invited to help pick one of the finalists by viewing short video pitches on YouTube, then liking and commenting on their favorite.

The full set of 23 semifinalist video pitches is available here: https://www.youtube.com/playlist?list=PLKPk8a4CmxhY.

“South Side Pitch is all about showcasing the wide-ranging small business scene on the South Side,” said Beth Kregor, the director of the Institute for Justice Clinic on Entrepreneurship at the University of Chicago. “This year’s semi-finalists have raised the bar. Anyone who wants to be inspired and informed about the South Side economy will want to see these videos, featuring chefs, scientists, inventors, artisans, fitness gurus, and so much more. By watching and choosing their favorites, the public selects one of the finalists, who is guaranteed to win exposure and a cash prize.”

South Side Pitch allows incredible entrepreneurs to share their success stories and the impacts their businesses have in a “Shark Tank” style contest, with the final contestants presenting their pitches during the live event on October 15. Applicants compete to win several great prizes, including over $38,000 in cash prizes. Like previous years, every finalist is guaranteed a prize.

Last year’s first-place winner, Runaway Cow, a vegan ice cream parlor in Bridgeport, 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 Polsky Center for Entrepreneurship and Innovation, the University of Chicago Office of Civic Engagement, United Airlines, and the Coleman Foundation.

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

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