The settlement that became Chester was first called "Finlandia" (the Latin name for Finland) and then "Upland" after the Swedish province of Uppland.

[19] In the 1700s and 1800s, Chester was a hub for business due to easy access to the Delaware River for the transport of raw materials and finished goods by ship.

[21] During the War of 1812, a group of volunteers from Chester called the Mifflin Guards was raised and led by Samuel Anderson.

The troops were sent to Fort DuPont to defend the Delaware River from the threatened attack of British Admiral George Cockburn but did not see any action.

In 1871, the Delaware River Iron Ship Building and Engine Works was opened by John Roach through the purchase of the Reaney, Son & Archbold shipyard.

[32] A four-day race riot that resulted in seven deaths broke out in the city in July 1917, and the separation of blacks and whites in Chester's neighborhoods and workplaces became more defined.

[33] In 1927, the Ford Motor Company opened the Chester Assembly factory on the site of the previous Roach and Merchant shipyard and built cars there until its closure in 1961.

Mayor James Gorbey issued "The Police Position to Preserve the Public Peace", a 10-point statement promising an immediate return to law and order.

[40] The demonstrations were marked by violence and police brutality[41] with Chester being dubbed the "Birmingham of the North" by civil rights activist James Farmer.

[40] Over 600 people were arrested over a two-month period of civil rights rallies, marches, pickets, boycotts, and sit-ins.

[42] National civil rights leaders such as Gloria Richardson, Malcolm X and Dick Gregory came to Chester in support of the demonstrations.

[43] Pennsylvania Governor William Scranton became involved in the negotiations and convinced the protestors to obey a court-ordered moratorium on demonstrations by agreeing to hold hearings on the de facto segregation of public schools in Chester.

Many bottom-rung projects were initiated in Chester, including the Westinghouse trash incinerator, a sewage treatment plant, and a prison.

The Wharf at Rivertown, a $60 million renovation of the Chester Waterside Station of the Philadelphia Electric Company, originally built in 1918, provides recreational and office space for businesses.

Located at a low elevation between Philadelphia and Wilmington, Delaware, Chester experiences a humid subtropical climate (Cfa.)

Roots defeated independent candidate Anita J. Littleton[67] in the November 2023 general election and was sworn into office on January 3, 2024.

In 1933, McClure was found guilty in federal court and sentenced to 18 months in prison for vice and rum-running,[73] but his conviction was overturned on appeal.

[74] In 1941, McClure was indicted for conspiracy to gain a $250,000 profit from the sale of the Chester Water Works to a private buyer.

The first non-machine mayor was elected in 1992:[28] Barbara Bohannan-Sheppard; however, in 1995, she lost her re-election bid and was replaced by Republican Aaron Wilson, Jr.

In the 1990s, the Pennsylvania Crime Commission reported that Chester's government had been dominated by "a triad of criminals, corrupt politicians and rogue law-enforcement officers" since the 1960s.

[76] John H. Nacrelli, the mayor of Chester from 1968 to 1979, was convicted of racketeering and income tax evasion for accepting $22,000 in bribes from an illegal gambling operation with ties to organized crime and served two years in prison.

[78] With the construction of Harrah's Philadelphia, the city received a series of horse races that were once held at the Brandywine Raceway and the now-defunct Liberty Bell Park Racetrack.

The racino opened on January 22, 2008, and features a specially constructed bridge that enables the midpoint of races, contested at one mile, to take place over the Delaware River.

Financing for the Rivertown development was announced in early 2008 by Governor Ed Rendell and Pennsylvania Senate Majority Leader Dominic Pileggi, with $25 million going to the construction of Subaru Park, and an additional $7 million towards a two-phase project composing of 186 townhouses, 25 apartments, 335,000 square feet (31,100 m2) of office space, a 200,000-square-foot (19,000 m2) convention center, more than 20,000 square feet (1,900 m2) of retail space, and a parking structure to house 1,350 cars.

The university offers associates, bachelors, masters, and doctoral degrees in areas ranging from traditional liberal arts to professional programs.

This widening and realignment project, spearheaded by the late State Senator Clarence D. Bell, allowed PA Route 291 to maintain at least two travel lanes in each direction.

US 13 follows Morton Avenue in the city's Sun Village section until it crosses Ridley Creek and becomes Chester Pike in Eddystone.

US 322 enters Chester from the northeast, merges with I-95 briefly and crosses the Delaware River over the Commodore Barry Bridge.

291 and the redevelopment of the Chester Waterfront, both the Delaware River Port Authority and PennDOT built a pair of entrance (westbound) and exit (eastbound) ramps to PA Rt.

Chester Police Department regularly requests support from neighboring municipalities for incidents occurring in the city.