Bridgeport is a working-class community on the near South Side – and one of the city’s oldest and most politically influential neighborhoods. Officially annexed by Chicago in 1863, the mayors who have hailed from Bridgeport represent almost 70 years of political clout, including Mayors Richard J. and Richard M. Daley.

In the shadow of Guaranteed Rate Field, Bridgeport is known for being home to World Series Champions, the Chicago White Sox. Bridgeport’s northern border is the south branch of the Chicago River, Pershing Road to the south, Bubbly Creek to the west and Stewart Avenue (Union Pacific Railroad) to the east.

Bridgeport got its name because of its proximity to a bridge on the Chicago River that was too low to allow safe passage for boats, so cargo had to be unloaded there. In the 1830s, large numbers of immigrants from Ireland started settling in this working-class neighborhood.

With a population of just over 30,000 Chicagoans, Bridgeport primarily offers single-family homes and new construction condos and townhomes. Bridgeport is a neighborhood with vibrant personality shining brightly through generations of hard work and rich history. Tall, leafy trees dot the streets, and wide-open parks are scattered throughout the neighborhood. Old churches still stand from the original immigrant settlers, and young families walk the same avenues their grandparents did. Bridgeport is a Chicago community of long-standing roots with a recent kick of modernization adding a contemporary twist to an old school neighborhood.

Homes in Bridgeport can be had for as little as $60,000 and there are some in the $1 to $1.5 million-plus range. But the bulk of Bridgeport single-family homes range from $150,000 to $600,000, while most condos fall between $130,000 and $350,000.

A great place to visit is Palmisano Park, formerly known as Stearns Quarry, transformed from coral reefs to quarry to landfill to park. Palmisano Park is truly a thing of beauty and not to be missed!

Bridgeport is sporting a refreshing indie vibe without having lost its solid, working class identity. From contemporary art to craft beer to upscale Chinese food, this Near South Side neighborhood is a gem.

Public transportation: CTA’s Orange Line at Halsted and Ashland. Or the Red Line at Sox/35th stop.

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