Healy School has been part of the Bridgeport community since about 1886. The school was named after an Irish immigrant. He immigrated to America in 1833 and came to Chicago in 1836. Moving to the Bridgeport area he farmed, raised stock, owned a limestone quarry, and Healy Slough. Before his death in 1871, he served as a School Director and Highway Commissioner.

The original school was built to alleviate overcrowding between its neighboring schools. It was a three story building with 15 classrooms. After the current Healy structure opened in 1960 the original building served as Richards Vocational High School for Girls.

The main building has two gyms, an auditorium, art room, computer lab, science labs, library and a lunchroom in addition to classrooms.

Overcrowding has always been an issue in the area; consequently, an Annex was built in 1993. The annex has 16 classrooms, a gym, library/media center, art room, and a lunchroom.

From the CPS alumni site, an article about the founder of Healy School,

From Men Who Have Made the Fifth Ward, by H.L. Schroeder and C.W. Forbrich, copyright 1894:

"The Healy School, named in honor of Robert Healy, one of the original patroons [a word meaning "a person who held an estate in land with certain manorial privileges granted under the old Dutch governments of New York and New Jersey (dictionary.com)] of the old Fifth Ward, was built in 1885 on Wallace Street, just north of Thirty-first Street. The 75 feet front cost the city but $6,000. The 15-room building consumed $48,000 more. January, 1886, it was opened to admit 525 pupils and ten teachers, Miss Jennie Dewey being the principal.... The Healy was a primary school -- sending all fifth year pupils to neighboring grammar schools to be prepared for high school. In September, 1893, it was made a grammar school, holding its pupils through eight grades. Its first class will graduate in June, 1897. In October, 1895, nine additional rooms were opened, having been added during the summer upon ground originally used as a yard and the twenty-five feet between the yard and alley, owned by Patrick Casey, sold for $3,200. The sum of $45,000 was devoted to the erection of these nine rooms and the rearrangement of basement to accommodate extra heating apparatus. The Healy now has 1,250 seats in twenty-four well-arranged class rooms, and a large German recitation room. One of its basement rooms is admirably adapted for manual training, and will doubtless be so utilized another year. Parents having boys of surplus vitality, whom they wish to continue in school will appreciate the value of such training.... The salaries of the twenty-nine teachers and engineer amount to $20,425 annually.