In 1884, Mr. Barney Kelly, the baggage master for the C. & N.W. Railway and a resident of the Township of Jefferson met the Chancellor of the Archdiocese of Chicago, Rev. Patrick Conway, on the train. (Jefferson was the name of locality where the parish now stands before the town was absorbed into Chicago in 1889.) Mr. Kelly spoke to Rev. Conway of the need for parish in that area. At the same time, a committee of people from the Maplewood, Avondale, and Cragin districts petitioned Archbishop Feehan to found a parish in the area. With the help of Rev. Conway, a representative from the Chancery was sent to the home of Mrs. Jane Byrne to attend a meeting of local Catholics interested in the establishment of a parish.
In response, Archbishop Feehan established a new parish to serve the people of Humboldt, Jefferson, Maplewood and Avondale. At that time, numerous farms and country land covered the area. There were no streetcars, few sidewalks, and few gravel streets. In March of that year, Rev. John J. Delaney was appointed the first pastor. The first masses were celebrated in the Fire Engine House on Stave Street. The first church proper was built by November of the same year on land purchased by Fr. Delaney at the corner of California and Shakespeare Avenues (now the location of the District 14 police headquarters). It cost $6,000. Fr. Delaney chose the name of St. Sylvester for the parish in honor of his father, Sylvester Delaney.
With Fr. Delaney’s death in 1889, a new pastor was appointed: Rev. Patrick Agnew. Rev. Agnew sold the property on California to the City of Chicago for use as a future police station and purchased the land at the corner of Richmond and Palmer. He also purchased land immediately on Humboldt Blvd. Together, these parcels form what is currently the land of the parish campus (with the exception of the current school).
It was under Rev. Michael O’Brien, who succeeded Rev. Agnew in 1897, that St. Sylvester would see the construction of most of the buildings still in use today. In 1899, Rev. O’Brien had a school built at the corner of Richmond and Palmer. Initially, the nuns occupied the upper floors of the building, but later moved to a residence across from the school as the parish and school enrollment grew. By 1907, with a growing population, a new church of Victorian Gothic style was started in 1906 and completed in 1907.
The one-hundredth anniversary of its dedication was celebrated on November 3, 2007. The rectory was built in 1911, Richmond Hall in 1913, and the convent in 1917. Even with the construction of the church, the interior was not yet complete. The new pastor Rev. Thomas J. Quinn, oversaw the installation of marble Gothic altars in 1926 to coincide with the International Eucharistic Congress that took place in Chicago.
As the years continued into World War II and after, the parish began to grow with the return of the soldiers from war. A redecoration of the church interior was completed in 1948. A few years later, with a burgeoning school population and an older building, the parish decided to build a new school. In 1955, The Schwinn family (of bicycle fame) donated land on the southwest corner of Humboldt and Palmer. The new school was completed two years later at a cost of $750,000. Soon after, in 1961, enrollment reached 1000 children. This building still serves the children of St. Sylvester today. (The old school was torn down and is the current site of the parking lot.)
The church building began to see some modification in the years after the Second Vatican Council. A freestanding altar was added, and later, in the seventies, the church interior was repainted in simple beige. It wasn't, however, until 1984 that significant remodeling was done under Rev. James Miller. A fire broke-out in the basement of the church due to an electrical short. While the damage was contained, repair was needed, and it was used as an opportunity to modify the interior of the church. The kneelers, side altars, communion rail, high pulpit, sedilia, and baptismal font were removed. A new freestanding altar, ambo, baptismal font, and presider chair were constructed. Additionally, the sanctuary was extended and interior of the church was repainted.
The way the church looks today, however, is the result of needed repairs in 1997. With the walls and floor in poor condition, the new pastor, Rev. Kevin Feeney, oversaw a repainting of the church and the installation of a new hardwood floor in conjunction with carpeting for the aisles and the sanctuary.
In 2007, at the 100th anniversary celebration, refurbished historic gothic candlesticks and a corresponding processional cross were added. Additionally, historic solid wood presider and deacon chairs were added in order to better complement the architecture of the building.