Milwaukee Alley & Public Plaza

Public Engagement, Streetscapes & Transporation

Milwaukee Alley

Upland Design reimagined an overlooked alley into a vibrant pocket urban plaza as one of the City of Chicago’s first alley-to-plaza transformations—demonstrating how small spaces can deliver big community impact. Located directly across from a busy transit station along Milwaukee Avenue in the Jefferson Park neighborhood, the project converted a formerly underused corridor into a welcoming, pedestrian-focused public space.

Despite its compact 14-foot width, the plaza was thoughtfully designed to feel open, active, and inviting. Community engagement played a central role in shaping the final design. Upland Design led numerous stakeholder meetings—hosted at local coffee shops, in the alley itself, and at the Park District field house—to gather input from residents, business owners, and community leaders. Multiple design concepts were explored, comparing materials, furnishings, and character to ensure the plaza reflected neighborhood priorities and identity.

Community feedback directly informed the selection of pavers, site furnishings, and overall aesthetic, resulting in a space that feels both authentic and well-crafted. Upland Design advanced the project through design approval and construction documentation, helping bring the vision to life.

The project illustrates Upland Design’s ability to pair creative placemaking with meaningful community collaboration—transforming tight urban spaces into memorable, people-centered destinations.

Project Details

CLIENT

Chicago Department of Transportation

PROJECT TYPE

Streetscape and Public Plaza

Role: Landscape Architect
Principal: Michelle Kelly
Design Lead:Liz Dafoe
Location: Chicago, Illinois
Services Provided: Master Planning and Design, construction documents