The 2nd Annual Work to Play Cup was a huge success! Thanks to all of the sponsors who made this one-of-a-kind event possible!
Work to Play Cup 2014


The 2nd Annual Work to Play Cup was a huge success! Thanks to all of the sponsors who made this one-of-a-kind event possible!

Funded by the Steans Family Foundation, Urban Initiatives’ summer 2026 Community Member to Coach program equipped 25 North Lawndale youth with paid coaching, financial literacy, and career development training while bringing together over 700 residents across four community play days.

This summer, Urban Initiatives’ Summer of Sport engaged 470 young people across 17 Chicago sites over five weeks, using sports sampling and intentional coaching to build skills like teamwork and resilience alongside strong attendance, safety, and enjoyment outcomes.

Urban Initiatives, in partnership with Chicago Public Schools, intends to apply for the FY27 21st Century Community Learning Centers grant to provide academic enrichment, sports and play programming, and family engagement opportunities across seven elementary schools.