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Chico ran for mayor again in the 2019 Chicago mayoral election.

Chico pursued a pre-medical degree at the University of Illinois at Urbana–Champaign, but after his sophomore year he transferred to the University of Illinois at Chicago. A political science major, he volunteered in the 11th Ward. He later secured an externship in the city's Department of Planning during his senior year, and he worked there from 1977 to 1980. He received his bachelor's degree in 1978. From 1980 to 1987, he worked for the City Council Finance Committee. Finance Committee chair Alderman Edward M. Burke promoted Chico to research manager, and he became senior research assistant for the Department of Planning and Economic Development. At that time, he took night classes at the Loyola University Chicago School of Law. He earned his J.D. degree in 1985 and became a member of the Loyola Law Review.

Chico served as the Chief of Staff to Mayor Richard M. Daley from 1992 to 1995, and board president of the Chicago Public Schools from 1995 to 2001. He was named Outstanding School Board President by the Illinois State Board of Education in 1997. From 2007 to 2010, he was board president of the Chicago Park District, and in 2010 he was board president of the City Colleges of Chicago. On June 7, 2011, Chico was named Chairman of the Illinois State Board of Education by Illinois Governor Pat Quinn.

Chico ran for Mayor of Chicago in the 2011 election, but was defeated by Rahm Emanuel. In late 2018, Chico declared a second bid for mayor in the 2019 election. After losing in the first round, he endorsed Lori Lightfoot.

Chico was named chairman of the Illinois State Board of Education in June 2011. His confirmation was delayed as a result of questions regarding his ties to the Save-A-Life Foundation, a failed charity that was undergoing investigation by Illinois Attorney General Lisa Madigan’s office.

In March 2010, Mayor Daley nominated Chico as chairman of the board of trustees of the City Colleges of Chicago and the board elected Chico chairman. Along with Chancellor Cheryl Hyman, Chico reformed the City Colleges budget by laying off 225 employees, removing unfilled jobs, and reducing executive spending to increase spending on technology and training for students. Furthermore, Chico and Hyman reduced taxation on property for two straight years, and cancelled nursing programs. He resigned 8 months later to run for Mayor of Chicago.

On September 27, 2010, Chico announced that he would run for mayor of Chicago in 2011. He was one of six candidates on the ballot.

In October 2007, Mayor Daley appointed Chico as president of the Chicago Park District Board of Commissioners. Chico supported the construction of a new soccer field in Lincoln Park despite opposition from local residents. In 2010, he stepped down.

In 2004, Chico, along with Planning Department colleague Marcus Nunes, formed the general practice law firm Chico & Nunes, which lobbies for clients seeking government business.

Chico also served as Special Counsel to Arnstein & Lehr in 2003 and 2004.

In 2004, Chico ran for the Democratic nomination to succeed retiring Republican U.S. Senator Peter Fitzgerald. He was the first Democrat to declare his candidacy, doing so on July 30, 2002, during a rally with Hispanic leaders. His Senate committee preferences included education, transportation, and judiciary. He also criticized the Bipartisan Campaign Reform Act and the No Child Left Behind Act, but supported gay marriage, abortion rights, stem cell research, the death penalty, and universal healthcare. Chico was the only candidate who supported gay marriage out of all seven Democrats and eight Republicans. Then-State Senator Barack Obama ultimately won the nomination over six other candidates including Chico.

Chico resigned as President of the Chicago Board of Education in 2001. He was succeeded in this office by Michael W. Scott.

In 1996, Chico left Sidley & Austin to become a senior partner of Altheimer & Gray. Oscar D’Angelo, a friend of Richard M. Daley and a former Altheimer partner, suggested to the firm’s managing partner that the firm hire Chico. In 2000, just four years later, at age 44, Chico became chairman of Altheimer. In 2002, the firm gave hundreds of thousands of dollars to Governor Rod Blagojevich and Attorney General Lisa Madigan's campaigns. In 2003, while Chico was chairman and simultaneously running for the US Senate, Altheimer became insolvent and dissolved. Some partners blamed the bankruptcy on poor management by Chico, while an attorney who sat on two financial committees blamed an economic downturn.

In 1995, the Illinois state legislature passed the Chicago School Reform Act, which gave the Mayor of Chicago unprecedented new control over Chicago Public Schools. Daley asked Chico to become the CEO, but Chico declined because he was resuming his law career. Chico instead recommended that Daley appoint colleague Paul Vallas as CEO, and Chico was named chairman of the School Reform Board of Trustees, which was renamed the "President of the Chicago Board of Education" in 1999 (the title which the board had originally held before 1995). In 1997 Chico was named Outstanding School Board President by the Illinois State Board of Education for his reforms in education and fiscal policies.

In 1991, Chico was a Deputy Chief of Staff for Mayor Richard M. Daley. He coordinated efforts to drain freight tunnels that were flooded with water from the Chicago River. Chico was later promoted to Chief of Staff, a position he held from 1992 to 1995. As part of his duties, he oversaw the completion of the International Terminal of O'Hare International Airport, preparations for the 1994 FIFA World Cup, and the construction of new schools. Along with Budget Director Paul Vallas, Chico helped add 1,000 officers to the police force and improved neighborhoods throughout the city through a program called Neighborhoods Alive.

Chico began working as an associate of the Chicago-based law firm Sidley Austin in 1987, and served as General Counsel to the Chicago Development Council, a real estate development association. He left the firm in 1991 to become the Deputy Chief of Staff for Mayor Richard M. Daley, but he later returned as partner in 1995 and 1996, leading the firm's practice related to state and local government.

Gery J. Chico (/ˈ ɡ ɛr i ˈ tʃ iː k oʊ / GERR -ee CHEE -koh; born August 24, 1956) is an American politician, Chicago lawyer, public official and former Democratic primary candidate for United States Senate.

Gery Chico was born on August 24, 1956, to a Mexican-American father, Jesse, and a Greek-Lithuanian mother, Jacqueline (née Kopulos). With his two younger brothers, he grew up in Chicago's McKinley Park neighborhood. His mother also worked as a secretary at the University of Illinois at Chicago College of Dentistry. Chico attended a now-closed parochial school, Our Lady of Good Counsel Catholic Elementary School at 35th and Hermitage, where he headed the altar boys and patrol boys, and also played baseball for two years. A hip injury kept him in a wheelchair during his freshman year at Thomas Kelly High School.

In the results of the election on February 22, Emanuel's 55% support dwarfed Chico's 24% support. Chico placed second. Chico won in 10 of Chicago's 50 wards, while Emanuel won 40. The campaign's communications director claimed that controversy over Emanuel's eligibility to run for mayor may have diverted the focus of the press away from the other candidates. After the election, Chico remained involved in the runoff elections for other city offices, endorsing a candidate for 25th Ward alderman.