Welcome to Englewood: A Neighborhood of Strength, History, and Resilient Rebirth

Tucked on Chicago’s South Side, Englewood is a community forged in history, tested by time, and rising with determination. Bordered by 55th Street to the north, 69th Street to the south, Ashland Avenue to the east, and Halsted Street to the west, this expansive neighborhood lies just 10 miles south of downtown — a place where legacy, culture, and transformation are reshaping the future, block by block.

Once a thriving commercial and cultural hub in the early 20th century, Englewood boasted one of the city’s busiest shopping districts, elegant homes, and a proud middle class. Though decades of disinvestment, economic shifts, and systemic challenges took a toll, Englewood has never lost its soul. Today, it’s a neighborhood where resilience meets revival — led by passionate residents, entrepreneurs, artists, and organizations committed to rebuilding with dignity and purpose.

A Legacy of Black Excellence and Community Pride

Englewood has long been a cornerstone of African American life in Chicago. During the Great Migration, it became home to teachers, doctors, business owners, and civic leaders who built institutions, raised families, and shaped South Side culture. The historic 63rd Street corridor once rivaled the Loop in retail energy — a legacy now being honored through new investment and community vision.

Today, Englewood remains a predominantly Black neighborhood with deep generational ties, strong churches, and a proud tradition of activism and self-reliance. Murals celebrate icons like Oprah Winfrey, who once lived here, and community leaders who’ve fought for justice, education, and equity.

Affordable Homes with Real Opportunity

One of Englewood’s greatest assets is its affordable housing stock — offering some of the most accessible homeownership opportunities in the city. You’ll find:

Stately greystone mansions and early 1900s two-flats
Classic brick bungalows with large lots
Renovated homes and new infill construction

With low property values and city-assisted programs for first-time buyers, Englewood presents a powerful chance to build wealth, stabilize communities, and be part of a grassroots renaissance.

Efforts like the Englewood Village redevelopment and community land trusts are helping ensure growth happens with residents, not over them.

Green Space, Culture & Innovation

Englewood is home to some of Chicago’s most ambitious revitalization projects:

The Englewood Arts Commons — a repurposed former bank turned creative hub for artists and makers
The CTA Green Line’s 63rd Street Station renovation — bringing modern transit and economic energy
Fresh Market at 61st & Cottage Grove — a full-service grocery store ending years of food insecurity
The proposed Englewood Botanic Garden — transforming vacant land into a world-class green space

Nearby Washington Park, designed by Frederick Law Olmsted, offers 372 acres of lagoons, walking paths, and historic architecture — a serene escape just minutes from home.

Transportation & Access

Despite its challenges, Englewood is well-connected:

Served by the CTA Green Line at multiple stations: Harvard, 63rd, and Damen
Multiple bus routes: #4 Cottage Grove, #55 Garfield, #111 O’Hare
Easy access to I-94 (the Dan Ryan Expressway) for car commuters

Residents are just 20 minutes from downtown, Midway Airport, and major employment centers.

A Community Rebuilding from Within

Change in Englewood isn’t coming solely from outside investors — it’s being led by locals. Organizations like:

Englewood Beautiful (beautification & safety)
The Woodlawn Conservancy (green jobs & urban farming)
Youth organizations and block clubs

…are planting gardens, cleaning streets, mentoring youth, and turning vacant lots into community assets.

Schools like Simeon Career Academy — home of legendary basketball alumni — continue to inspire excellence, while new charter networks and adult education programs are expanding opportunity.

More Than a Comeback — A Reclamation of Hope

Englewood doesn’t need pity.
It needs partnership, respect, and investment — and it’s ready to deliver returns in community strength, cultural richness, and untapped potential.

This is a neighborhood where a mural tells a story of survival, where elders watch over the block, and where every painted house, new business, or child playing outside is a victory.