As of the census of 2000, there were 36,854 people, 12,814 households, and 8,124 families residing in the city. The population density was 7,605.4 people per square mile (2,933.9/km²). There were 14,976 housing units at an average density of 3,090.5/sq mi (1,192.2/km²). The racial makeup of the city was 18.94% White, 75.70% African American, 0.20% Native American, 0.61% Asian, 0.01% Pacific Islander, 3.03% from other races, and 1.51% from two or more races. Hispanic or Latino of any race were 5.39% of the population.
There were 12,814 households out of which 32.7% had children under the age of 18 living with them, 24.8% were married couples living together, 32.1% had a female householder with no husband present, and 36.6% were non-families. 31.2% of all households were made up of individuals and 11.2% had someone living alone who was 65 years of age or older. The average household size was 2.64 and the average family size was 3.34.
In the city the population was spread out with 29.8% under the age of 18, 13.0% from 18 to 24, 26.8% from 25 to 44, 18.6% from 45 to 64, and 11.8% who were 65 years of age or older. The median age was 31 years. For every 100 females there were 89.1 males. For every 100 females age 18 and over, there were 84.7 males.
The median income for a household in the city was $23,703, and the median income for a family was $29,436. Males had a median income of $29,528 versus $21,005 for females. The per capita income for the city was $9,052. About 22.8% of families and 27.2% of the population were below the poverty line, including 36.9% of those under age 18 and 21.8% of those age 65 or over.
In Chester, east-west streets are numbered, while north-south streets carry names. The main bisecting street, known as The Avenue of the States south of 9th Street and Edgmont Avenue north of it, is signed as both Pennsylvania Route 320 (southbound only; northbound PA Rt. 320 uses adjacent Madison Street to Interstate 95) and Pennsylvania Route 352. North of I-95, State Route 320 follows Providence Avenue. Between 1993 and 2006, the Pennsylvania Department of Transportation (PennDOT) widened and realigned Pennsylvania Route 291 from Trainer to Eddystone from a two-lane roadway to a five-lane roadway. This widening and realignment project, spearheaded by the late State Senator Clarence D. Bell of Upland, allows PA Route 291 to maintain at least two travel lanes in each direct between the refinery towns of Marcus Hook and Trainer and the Philadelphia International Airport, as well as promote the riverfront development in the city. Prior to the realignment, which was done first, the roadway followed 2nd Street to Crosby Street, then bore right onto E. 4th Street, widening to four lanes and becoming the "Industrial Highway" in Eddystone. Post-realignment, the road now follows W. 2nd Street to Concord Avenue, becoming the "Industrial Highway" past Concord Avenue and bypassing the Kimberly-Clark (formerly Scott Paper) processing facility.
In addition to State Rt. 291, Chester is served by two interstate highways: Interstate 95 and Interstate 476, which meet in nearby Eddystone. I-95 was built in the 1960s and originally terminated just north of the Chester/Eddystone line at the present-day I-95/I-476 junction. It was extended north in the 1970s with the section around Philadelphia International Airport being completed in 1985. Three exits on I-95 allow access to Highland Avenue, Kerlin Street, and The Avenue of the States (Rts. 320 & 352), with access to Widener University, via State Rt. 320. Of the three, only Kerlin Street is a partial exit, although the Avenue of the States exit was also a partial exit until the completion of a southbound on-ramp, also spearheaded by the late State Sen. Bell, was completed in 2002. I-476, planned as an alternative route to State Rt. 320 since the 1920s and an original planned extension of the Pennsylvania Turnpike in the 1950s (as part of the 1,000-mile (1,600 km) Turnpike network), was finally opened to traffic in 1992. An exit at MacDade Boulevard (which becomes 22nd Street in Chester) allows access to I-476 without having to use I-95.
Two federal highway routes, U.S. Route 13 and U.S. Route 322, also run through Chester. U.S. Rt. 13 enters Chester from Trainer on W. 4th Street, becomes part of Highland Avenue between W. 4th St. and W. 9th Street, and then continues on 9th Street to Morton Avenue. U.S. Rt. 13 follows Morton Avenue in the city's Sun Village section until it crosses Ridley Creek and becomes Chester Pike in Eddystone.
U.S. Rt. 322 enters Chester as a part of I-95 (merging on at Highland Avenue) and then departs I-95 at the Commodore Barry Bridge exit. Prior to the bridge's opening in 1974, U.S. Rt. 322 would cross the Delaware River on the Chester-Bridgeport Ferry, via Flower Street, causing major backups because of limited space on the ferries. With the expansion of State Rt. 291 and the redevelopment of the Chester Waterfront, both the Delaware River Port Authority and PennDOT have plans in place to start construction of new exit and entrance ramps from the bridge to Rt. 291, providing an alternate route to the Chester Waterfront.
In addition, talks have taken place for the reconstruction of U.S. Rt. 322 from a two-lane road to a four-lane road between Chester and U.S. 1 in Concordville, Pennsylvania, and the Highland Avenue exit. The road currently requires traffic to merge onto I-95 in the left lane and requires changing lanes three times to the Commodore Barry Bridge exit ramp in less than a mile. Such a major undertaking would result in the demolition of numerous homes in the city's crime-plagued Highland Gardens section, along with condemning properties in nearby Chester Township, as I-95 passes through both municipalities between U.S. Rt. 322 and the Commodore Barry Bridge.
Chester is served by SEPTA (South Eastern Pennsylvania Transit Authority) via seven bus routes, all of which either terminate at or pass through Chester Transportation Center, a transportation hub in the Business District that also serves as a stop on the SEPTA R2 Marcus Hook/Wilmington/Newark rail line using Amtrak's Northeast Corridor. The R2 also makes a stop at the Highland Avenue station and, prior to 2003, also stopped at Lamokin Street at the junction of the NEC and the abandoned Penn Central Chester Creek Secondary Branch.