17th Annual Woodlawn Community Summit

DEEP ROOTS, STRONG FUTURE

Saturday, March 7, 2026

This is a special invitation to reunite our neighbors, stakeholders and business leaders to celebrate the 17th Annual Woodlawn Community Summit and take a fresh look at economic development, sustainability, and housing.

Join us as we continue this journey of engagement and community leadership with those who live, work and invest in Woodlawn.

-- COFFEE & CONVERSATIONS --

Meet and Greet

Enjoy the opportunity to connect with neighbors, community leaders and elected officials before the opening session begins.

-- OPENING SESSION --

Deep Roots, Strong Future: The South Side’s Path Forward

This session highlights new and emerging developments shaping Chicago’s South Side and what they mean for the future of community planning. Speakers and community voices will reflect on the South Side’s legacy of leadership, creativity, and collective action, while examining pathways to equitable development that honor residents, preserve culture, and invest in long-term neighborhood stability. Grounded in the area’s rich history and neighborhood identity, attendees will hear insights on upcoming projects, evolving planning approaches, and strategies for building community-led progress rooted in place and possibility.

-- BREAKOUT SESSIONS --

Housing

Rent and Housing Affordability Trends in Woodlawn: Reality vs. Perception

Housing costs in Woodlawn are changing, and many residents are feeling it. Rents have increased over the past few years, and there is a growing gap between what people think is happening and what the numbers actually show. This community conversation is a chance to talk openly about affordability, stability, and what it means for neighbors who live and work here.

We will look at current rent levels in Woodlawn, how they have shifted recently, and how many households are spending more than they can afford on housing. We will also discuss practical options that exist today, including new buyers programs, commercial rental and purchase, and long-term tools that help keep housing within reach.

You will hear from residential and commercial brokers and a local developer who are actively working in the Woodlawn market.

Economic Development

Navigating Uncertainty: Practical Strategies for Small Business Growth

This workshop is designed to help small business owners adapt and grow during uncertain economic times. Rather than focusing on predicting every challenge, the session emphasizes making thoughtful, practical decisions using available resources that build long-term stability.

Through guided conversations with experienced speakers, the workshop will highlight key challenges and strategies relevant to both newer businesses and more established companies. Topics will include responding to economic shifts, changing customer behavior, workforce challenges, managing cash flow, planning ahead, and building trusted relationships with advisors and partners.

By bringing together different perspectives and stages of experience, this session helps connect agility with experience and provides participants with clear, actionable ideas to turn today’s challenges into tomorrow’s opportunities.

Sustainability

Blacks in Green Overview:

The People’s History of Woodlawn! YOUR STORY, YOUR GLORY!

Join this 90-minute immersive, neighbor-driven launch experience where Woodlawn residents and friends don’t just learn local history—they build it together in real time! Through a high-energy, joy-filled format that blends community storytelling, live vision-boarding, and gamified civic pride ~ participants can make short video memories in the BIG Story Booth…design clues for the “Woodlawn: Place of Pioneers” treasure hunt this summer…map out South Lakefront wayfinding signage installs…or quilt-up icons of history, home, and hope for exhibition at the Woodlawn & South Lakefront Visitors Center this spring! This kickoff turns Woodlawn’s people, places, and defining moments into a celebration of our Great Migration roots and sustainable economic future. Grab a passport and hit the road with Blacks in Green on this epic hunt for history!

Community Partnerships

Engaging with the University: Building Connections for a Stronger Woodlawn

Explore how the Woodlawn community can connect with the University of Chicago through opportunities in health, safety, arts and culture, education, and economic development. This interactive session highlights pathways for engagement, access to shared resources, and collaboration—inviting residents to be part of shaping a strong and inclusive future for Woodlawn.

-- RELEASE --

By registering for this event, you authorize The Woodlawn Community Summit to use your name, statements and likeness, without charge, for promotional purposes in program promotion, publications, advertising, video, web, news media, or other formats.

Know what’s Happening Next — before everyone else does.

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Host or Publisher Woodlawn Community Summit Organizing Committee