The Chicago Sky is taking big steps to support women entrepreneurs in the city. Through its Foundation’s Women’s Small Business Cohort, the team offers mentorship, workshops, and up to $30,000 in funding to help women-led businesses grow.
Their ongoing #RedefinePossible initiative also connects local female leaders through events like leadership brunches and mentorship programs, impacting over 600 women since 2016.
According to ABC News, the 2025 cohort will consist of eight women-owned businesses. The first-place winner will receive $30,000, the second-place winner will get $20,000, and the third-place winner will receive $15,000. The remaining five businesses in the cohort will each receive $5,000.
By combining financial support with community engagement, the Chicago Sky continues to uplift women in business and inspire the next generation of leaders in Chicago.
To apply for the 2025 Chicago Sky small business cohort, click here.

