Bridgeport

Discover the Heart of Chicago’s South Side in Bridgeport — A Proud, Diverse Neighborhood Blending Artistic Energy, Historic Roots, and Community Spirit.

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Location

South Side. Bounded by the Stevenson Expressway (North), Pershing Road (South), Halsted Street (East), and Ashland Avenue (West).

Vibe

Authentic, historic, humble, and increasingly artistic. Strong neighborhood pride with a growing creative energy.

Commute

10–15 to downtown via Orange Line

Average Value

$410,000

Perfect for

Artists, longtime locals, first-time buyers, and those seeking an authentic Chicago neighborhood with a mix of tradition and growth.

Overview

Transit

Subway

Bridgeport

Bus

CTA routes: #8 Halsted, #35 31st/35th Street, #44 Wallace/Racine

Airport

O'Hare – 55-65 mins | Midway – 20-25 mins

A historic, blue-collar neighborhood with deep roots and a growing creative scene.

Bridgeport is one of Chicago’s oldest and most storied neighborhoods, known for its working-class heritage, political history, and growing arts and food scenes. Located just southwest of the Loop, it has traditionally been home to Irish, Italian, and Lithuanian immigrant families, and more recently has become a diverse and evolving community. Bridgeport balances its strong sense of tradition with modern touches — local galleries, microbreweries, and new restaurants continue to open while historic churches, parks, and rowhomes ground the neighborhood in its past. 🌳 Parks, Dining & Culture Outdoor: McGuane Park (fields, pool), Palmisano Park (hiking trails, nature), nearby Canal Origins Park Dining: Maria’s Packaged Goods & Community Bar, Zaytune Mediterranean Grill, Bridgeport Bakery 2.0 Culture: Bridgeport Art Center, Zhou B Art Center, local galleries and community festivals 🏫 Schools & Essentials Schools: Bridgeport Catholic Academy, Haines Elementary, De La Salle Institute Essentials: Aldi, Walgreens, local grocers and delis Good walkability, improving bike infrastructure, easy car access to expressways Close to Guaranteed Rate Field (White Sox Stadium)

Gallery