Annual South Side Pitch Competition

Two presenters on stage beside a Tawney Coffee slide, judges seated nearby, audience watching

Stay Tuned to Save Your Seat for 13th Annual South Side Pitch!

Every year, small businesses across the South Side of Chicago participate in South Side Pitch, sharing stories about their roots, their impact, and their visions for the future. This year the competition will not be live streamed so make sure to save your seat before spots run out!

October 15, 2026
6:00pm

Doors Open & Networking

Polsky Exchange North Center, 1452 E 53rd St 2nd Floor. Chicago, IL 60615

6:20pm

Opening Introduction

Beth Kregor, IJ Clinic on Entrepreneurship Director

6:30pm

Keynote

To be announced in September 2025

6:45pm

Pitch Competition

Information on finalists to pitch will be provided once announced in September 2026!

8:00pm

Voting & Reception

Cast your vote for your favorite pitches!

8:25pm

Winners Announced!

Prizes

With over $40,000 in prizes, the IJ Clinic is spotlighting South Siders with a passion to pitch. Compete against over 100 applicants for one of the top five spots! Each finalist is guaranteed a cash prize at the end of the night.

First Place

$15,000

Second Place

$10,000

Third Place

$6,000

Fourth Place

$3,000

Fifth Place

$1,500

Audience Favorite Award

$1,500

South Side Sensation

$3,000

*The Rustandy Center Social Impact Award is a generous cash award of $2,500 that is given to a South Side Pitch finalist chosen by staff from the Rustandy Center for Social Sector Innovation at the University of Chicago Booth School of Business.

*The Audience Favorite award is a cash award chosen by the audience that acknowledges the South Side Pitch finalist that receives the highest score for their pitch.

*The South Side Sensation award is a cash award chosen by the audience that acknowledges the South Side Pitch finalist that demonstrates exemplary social impact and showmanship for their business as a South Side resident.