Historically, much of the neighborhood was an Irish-American enclave. In the 1830s, large numbers of immigrants from Ireland started settling in this working-class neighborhood. Many of the same Irish immigrants who helped build the Erie Canal later came to Chicago to work on the Illinois and Michigan Canal. Because of inadequate funding for the project, the State of Illinois began issuing "Land Scrip" to the workers rather than paying them with money. A large number of those Irish-Americans who received the scrip used it to purchase canal-owned land at the northern end of the canal where it meets the south branch of the Chicago River. The original Bridgeport village, named "Hardscrabble," centered here on what is now the diagonal section of Throop Street[1] on the northwest side of the Bridgeport community area. The area later became known as Bridgeport 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. Finley Peter Dunne later wrote about this area in popular sketches around the turn of the 20th century. His Mr. Dooley character lived on "Archey Road" (present day Archer Avenue, Chicago) in Bridgeport. See also South Side Irish. Bridgeport is also home to many Italian Americans like its smaller neighbor to the east, Armour Square.

Although the Irish are Bridgeport's oldest and most famous ethnic group (besides the Lebanese), Bridgeport has also been home to a large number of other groups. Many Lithuanian-Americans settled along Lituanica Avenue, which runs between 31st Street and 38th Place one block west of Halsted Street in what was once called "Lithuanian Downtown" and the center of Lithuanian settlement in Chicago . Today, there are also large numbers of first and second generation Mexican-Americans and Chinese-American who, like the Irish immigrants of the 19th century, have settled in the Bridgeport area due to its affordable housing and proximity to their work.

Bridgeport's Polish history can be seen in its two churches in the Polish Cathedral style: St. Mary of Perpetual Help, and St. Barbara. The Art Institute of Chicago has done restoration work on the paintings in the Shrine Altars at St. Mary of Perpetual Help which date back to 1890, with further plans calling for restoration of the stained glass windows and to complete the painting of the interior ceilings and rotunda. The influence of other Eastern European immigrants to Bridgeport is evident at St. Jerome Croatian Catholic Church, which holds services in both Croatian and English.

Bridgeport has long been one of the city's political hotbeds, having been home to five of Chicago's 45 mayors. They are, in order of service: Edward Kelly, Martin Kennelly, Richard J. Daley, Michael Bilandic, and Richard M. Daley. The most prominent example of the neighborhood's influence on Chicago politics is illustrated by a 46-year long stretch (1933–1979) in which a Bridgeport native held the city's highest office. The current (as of 2010) mayor Daley no longer resides in Bridgeport.