10 Races to Watch in Chicago's Municipal Runoff Elections

With Chicago Mayor Rahm Emanuel stepping aside, and a number of challengers vying for aldermanic seats, City Council could look quite different after the Apr. 2 municipal runoff elections. Here's a look at 10 big races happening across the city.

11 photos
With Chicago Mayor Rahm Emanuel stepping aside, and a number of challengers vying for aldermanic seats, City Council could look quite different after the Apr. 2 municipal runoff elections. Here's a look at 10 big races happening across the city —
No matter who wins the April runoff election, Chicago's next mayor will be an African-American woman for the first time in the city's history. Lori Lightfoot and Toni Preckwinkle both advanced to the runoff election, garnering 17.5 percent and 16 percent of the vote, respectively. They prevailed over 12 other candidates in the most crowded field of mayoral hopefuls in Chicago history, a field that grew after outgoing Mayor Rahm Emanuel announced in September that he would not run for a third term.
Lightfoot is the former president of the Chicago Police Board. Emanuel appointed Lightfoot to head the board in 2015, and to chair the Police Accountability Task Force in 2016, in the wake of the fatal shooting of Laquan McDonald. A former federal prosecutor from 1996 to 2002, Lightfoot has also held various roles in city government, including as chief of staff for Chicago’s Office of Emergency Management and Communications in 2005. She most recently was a partner at Mayer Brown LLP and entered the race before Emanuel dropped out - criticizing the candidates, including Preckwinkle, who launched their bids after his announcement. A late surge, seemingly fueled by an endorsement from the Chicago Sun-Times and other candidates' perceived ties to the so-called "machine," was enough to put Lightfoot at the top.
Preckwinkle is the current Cook County Board President and chair of the Cook County Democratic Party. Long seen as one of the most viable challengers to Emanuel, Preckwinkle has been board president since 2010, and prior to that was elected to five terms as alderman of the 4th Ward on the city's South Side. In April 2018, she became chair of the Cook County Democratic Party. She enjoys significant support from organized labor, particularly Service Employees International Union Local 1 and the Chicago Teachers Union.
The race has been contentious from the start, with both candidates on the attack as each touts her progressive credentials. Lightfoot has painted Preckwinkle as a politician entrenched in the so-called "machine," while Preckwinkle has highlight Lightfoot's background as a "wealthy corporate lawyer" who's worked for Wall Street. A victory by either woman would be historic in more ways than one. Both in contention to be Chicago's first black female mayor, Lightfoot would also be the city's first openly-LGBTQ mayor, while Preckwinkle would be the first mayor to chair the Cook County Democratic Party since Richard J. Daley.
Melissa Conyears-Ervin and Ameya Pawar will face off once again in the runoff election for Chicago treasurer. Conyears-Ervin earned 44.3 percent of the vote, while Pawar earned 41.6 percent in the Feb. 26 match, according to the Chicago Board of Elections. Those totals were not enough for either candidate to reach the 50 percent threshold to win the election outright, sending them to the runoff over the third candidate Peter Gariepy, who earned 14.2 percent of the vote.
Conyears-Ervin is currently an Illinois state representative, serving the 10th District since 2017. She has a master’s degree in business administration from Roosevelt University and has garnered some key endorsements, from the likes of SEIU Local 73, the Chicago Teachers Union, and Illinois Secretary of State Jesse White, as well as Gariepy, her former opponent. She is married to 28th Ward Ald. Jason Ervin.
Pawar is currently the 47th Ward alderman, running for a new office after vowing to only serve two terms on City Council. He ran on a progressive platform for Illinois governor last year, but dropped out of the Democratic primary early on, citing a prohibitive lack of funding. He’s floated the idea of creating a publicly-owned bank, which would aim to provide low-interest loans for residents and would essentially cut private banks out of the business of handling the city’s finances. His progressive approach to ethics and transparency in particular has earned him the endorsements of both the Chicago Tribune and the Chicago Sun-Times, as well as SEIU Local 1 and Rep. Mike Quigley.
The two will square off in April for the open position vacated by current Chicago Treasurer Kurt Summer. Summers, often seen as a rising political star, unexpectedly announced in 2018 that he would not seek re-election. He was Cook County Board President Toni Preckwinkle’s ex-chief of staff and served just one term. The position of treasurer can be seen as the city’s accountant, managing Chicago’s operating funds, controlling the city’s investments and overseeing the city’s increasingly-troubled pension funds.
Ald. Leslie Hairston is headed to a runoff against a prominent activist in the 5th Ward on Chicago's South Side. Hairston earned 48.5 percent of the vote against two opponents in the Feb. 26 election. Community activist William Calloway came in second place with 26.7 percent, meaning the two will square off once again in April.
Calloway is credited with pushing for the release of dashcam video showing Chicago Police Officer Jason Van Dyke shooting Laquan McDonald 16 times in 2014. The release of the footage made international headlines and set off a series of events that included the ouster of the Chicago police superintendent, a second-degree murder conviction for Van Dyke and a U.S. Department of Justice investigation that prompted a series of reforms under a new consent decree. Calloway is a documentary filmmaker who founded Christianaire, a violence prevention nonprofit organization, and previously ran for Illinois state representative for the 25th district in 2018, falling short in the Democratic primary.
An attorney who was first elected in 1999, Hairston has highlighted her membership in the City Council's Progressive Reform Caucus and touted her experience working on infrastructure and business development in the ward, like a multimillion-dollar reconstruction of South Lake Shore Drive, renovations to the South Shore Cultural Center, construction of the Comer Children’s Hospital and more.
A major issue in the race where the candidates differ is their approach to the forthcoming Obama Presidential Center, slated for construction in the ward's Jackson Park, to be completed by 2021. Hairston has said she opposes a community benefits agreement between developers and residents to guarantee jobs at the center to area residents and protect them from being displaced by the development. Calloway has expressed support for such an agreement to be made with the Obama Foundation, the City of Chicago and the University of Chicago. The 5th Ward includes parts of the Hyde Park, Jackson Park, South Shore and Greater Grand Crossing neighborhoods.
One of the largest field of aldermanic candidates in the city last round has whittled to two in the runoff election for the 20th Ward. Jeanette Taylor and Nicole Johnson emerged victorious from the initial nine candidates vying to replace Ald. Willie Cochran, who was indicted on federal criminal charges in December 2016. Taylor garnered 28.8 percent of the vote in the Feb. 26 election, while Johnson earned 22 percent.
Taylor is a community activist who led a 34-day hunger strike to stop the closing of Dyett High School and has advocated for a community benefits agreement for the Obama Presidential Center, a proposal Johnson has also said she supports. Johnson is an education consultant and has worked as a policy and program manager at Chicago Votes, as well as for Sen. Dick Durbin, among other elected officials.
Both are looking to succeed Cochran, who was charged with a total of 11 counts of wire fraud, two counts of federal program bribery and two counts of extortion. Authorities allege Cochran, a former Chicago police officer, solicited bribes from area businesses and used money from a charitable fund in part to pay for his daughter’s college tuition and roughly $25,000 on gambling at casinos. Cochran originally entered a plea of not guilty in 2016, then rejected a plea deal in 2018, before ultimately pleading guilty on March 21 and resigning his seat.
He had previously announced in 2017 that he would not run again, though he said his decision had nothing to do with his indictment. Cochran is the third 20th Ward alderman to face charges, with two of his predecessors - Cliff Kelley and Arenda Troutman - imprisoned for fraud. The ward includes parts of the Woodlawn, Back of the Yards, Canaryville, Washington Park and Englewood neighborhoods on the city’s South Side.
The race to replace 25th Ward Ald. Danny Solis has gotten heated. Byron Sigcho-Lopez and Alex Acevedo topped the field of five candidates on Feb. 26, with 29.2 and 22.1 percent of the vote, respectively.
Sigcho-Lopez is an educator and public policy researcher at the University of Illinois-Chicago, who has previously worked as the director of the Pilsen Alliance, an organization focused on social justice for working class and immigrant communities on the Lower West Side. A Democratic Socialist, he was one of four candidates who previously challenged Solis in 2015, coming in second with 19 percent of the vote - falling about 80 votes short of forcing Solis into a run-off election.
Acevedo is a registered nurse who has previously worked as a community relations manager at Oak Street Health, a clinic for senior citizens. He is the son of former state Rep. Eddie Acevedo and unsuccessfully ran for his father’s seat in the state legislature in 2016. Both candidates currently sit on local school councils for schools in the community.
This race has been plagued by plenty of controversy, one of which was allegations of vote-buying. On March 11, Acevedo said he identified workers for Sigcho-Lopez's campaign handing out gift cards on the Feb. 26 election day, with a Chinatown polling place official corroborating the accusation. Sigcho-Lopez categorically denied employing any vote-buying tactics and in turn accused Acevedo of a "desperate 11th hour attempt to mislead and distract voters." The Chicago Board of Elections opened an investigation into the "extremely serious" vote-buying allegation and said it would devote "additional resources" to the ward for the runoff election.
The 25th Ward is no stranger to controversy. Outgoing Ald. Danny Solis has gone silent since late January, when the Chicago Sun-Times reported that he secretly recorded conversations with embattled Ald. Ed Burke as part of a criminal investigation that resulted in a charge of attempted extortion against Burke on Jan. 3. Solis himself became the subject of a federal criminal investigation in 2014, according to a source familiar with the probe, which is why Solis cooperated in the investigation into Burke. No charges have been filed against Solis, who resigned from his position as chair of the powerful City Council Committee on Zoning, Landmarks and Building Standards, which votes on where developers can build multi-million to multi-billion dollar projects across the city.
Solis has represented the ward since he was appointed in 1996, meaning this election will mark the first time in nearly a quarter-century that the 25th Ward - which includes parts of the Lower West Side, Pilsen, Greek Town, Chinatown and University Village neighborhoods - will have a new voice on City Council. Both candidates are about half the age of 70-year-old Solis, meaning that no matter who wins, the 25th Ward will also for the first time be represented by a millennial. Solis was a major flash-point in the race, as the candidates for the 25th Ward have attempted to distance themselves from him and paint themselves as reformers.
Separated by just 27 votes in the first round, the longtime 30th Ward alderman is headed to a runoff against the daughter of a former congressman. Incumbent Ald. Ariel Reboyras finished the Feb. 26 election ahead of Jessica Gutierrez by a razor-thin margin, setting the stage for the two to face off once more. The election pits two longtime allies of outgoing Mayor Rahm Emanuel against one another.
Reboyras chairs the City Council Committee on Public Safety, which oversees the Chicago Police Department, and has backed Emanuel’s agenda items on multiple occasions, including police reform. Emanuel offered Reboyras his support at a fundraiser in September, according to a video Reboyras posted on his Facebook page, in which Emanuel gave Reboyras credit for bringing a new elementary school to the Belmont-Cragin neighborhood. Reboyras, who was first elected in 2003, also earned the endorsements of the Chicago Tribune and the Chicago Sun-Times.
Jessica Gutierrez is daughter of former Rep. Luis Gutierrez, another Emanuel ally who chaired the mayor's re-election campaign in 2015. Luis Gutierrez announced in 2017 that he would not seek re-election the following year, engineering the victory of his chosen successor, now-Rep. Jesus “Chuy” Garcia - who was Emanuel’s mayoral opponent in 2015. Jessica Gutierrez most recently worked as a field director on Garcia’s Democratic primary campaign for her father’s Congressional seat. She ran to Reboyras’ left, with the Chicago Teachers Union’s endorsement, a vow to join the Progressive Caucus, and hope that Emanuel’s support would prove detrimental to Reboyras.
The 30th Ward includes parts of the Belmont-Cragin, Portage Park and Irving Park neighborhoods on Chicago’s Northwest Side.
After avoiding it by the slimmest of margins in her last election, Ald. Deb Mell is headed to a runoff election against Rossana Rodriguez-Sanchez in Chicago's 33rd Ward. Rodriguez-Sanchez took 42.1 percent of the vote and Mell earned 41.3 percent, separated by a margin of 83 votes, with a third candidate playing spoiler to send them to a runoff.
Mell ran for the first time in 2015 to defend her appointment to her father’s old seat, avoiding a runoff election by 17 votes, the slimmest of leads that materialized thanks to absentee ballots counted after Election Day. This time around, she faced perhaps an even tougher challenge from Rodriguez-Sanchez - a Democratic Socialist that the Chicago Reader said could be “the next Alexandria Ocasio-Cortez.”
Rodriguez-Sanchez is a Puerto Rican activist who currently works as an internship and career adviser for theater and dance at Columbia College. When Mell’s last opponent Tim Meegan, a member of the Chicago Teachers Union, lost in 2015, the remnants of his campaign operation - including Rodriguez-Sanchez, a founding member - turned into the 33rd Ward Working Families independent political organization. That organization is, in part, what propelled Rodriguez-Sanchez’s campaign, plus the backing of unions like CTU and SEIU.
Mell’s father Dick Mell was once the Northwest Side kingmaker, as 33rd Ward alderman beginning in 1975, the ward’s Democratic committeeman starting the following year and the father-in-law of disgraced Gov. Rod Blagojevich. After 38 years, Dick Mell resigned as alderman in 2013, and Mayor Rahm Emanuel appointed his daughter - then a state representative in her third term - to fill his seat. He lost his position as the ward’s Democratic committeeman in 2016, meaning this time around, he wasn't able to give his successor as big of a boost. This time, Deb Mell earned the endorsement of the Chicago Tribune and the Chicago Sun-Times, which pointed to her upgrades to parks in the ward and her “more progressive-leaning voice” on the City Council.
Seemingly the most important issue in the 33rd Ward - which includes parts of the Albany Park, Irving Park, Avondale and Ravenswood Manor neighborhoods - is affordable housing.
Chicago's second longest-serving alderman is headed to a runoff in a race that's been rife with controversy in the 40th Ward on the city's Far North Side.
Ald. Pat O'Connor is Mayor Rahm Emanuel's floor leader who succeeded Ald. Ed Burke as chair of the powerful City Council Committee on Finance when Burke was forced out amid a corruption charge. O'Connor was first elected in 1983 and, along with Burke, is one of the last two remaining City Council members who were part of the "Vrdolyak 29," a majority-white group of aldermen who stymied the agenda of Mayor Harold Washington, Chicago's first black mayor, in the 1980s. O'Connor - who had previously floated the possibility of retiring - earned 33.3 percent of the vote against four other candidates in the Feb. 26 election, and will now face Andre Vasquez, who took 20.1 percent of the vote, in the runoff election.
Currently working as a senior manager for AT&T, Vasquez is a Democratic Socialist who has said he got seriously involved in politics when he backed Sen. Bernie Sanders for president in the 2016 Democratic primary. He now chairs the North Chapter of Reclaim Chicago and has been endorsed by several progressive organizations and officials, as well as unions like the Chicago Teachers Union, Service Employees International Union Local 73, and more.
The race has seen some controversy, as Vasquez was a rapper under the stage name "Prime" in the late 1990s and early 2000s. O'Connor's campaign unveiled a website ahead of the runoff, documenting Vasquez's history of misogynistic and homophobic remarks made in hip-hop forums or in his lyrics. Vasquez said in a statement that he's "not proud" of who he was when he made this comments, between 2001 and 2010, but that "some people grow and learn and change." He also pointed to a racial controversy surrounding O'Connor, highlighting his opponent's remarks at an October forum with all five original candidates, in which O'Connor attacked one of his challengers, Ugo Okere, for a fundraising invitation that advertised "building Nigerian political power." O'Connor's criticisms, in part saying the flier "doesn't talk about community," drew boos from the crowd and widespread condemnation from the candidates as well as the forum moderator, who later tweeted that O'Connor was "a racist troll."
The 40th Ward includes parts of the city's West Ridge, Andersonville, Bowmanville, Ravenswood and Edgewater neighborhoods.
Ald. James Cappleman is headed to a runoff election against a scientist in the 46th Ward on Chicago's North Side. Cappleman won 44.1 percent of the vote against five other candidates, with Marianne Lalonde coming in second with 18.1 percent, sending them both to the April runoff.
Cappleman is a former social worker who was first elected in 2011 and touts his work on developments in the ward, including the renovation of the CTA's Wilson Station, the rehabilitation of the Uptown Theatre and the introduction of new businesses.
Lalonde is a scientific research consultant with a Ph.D in chemistry who has worked on Capitol Hill and has lived in Uptown for three years. Running to Cappleman's left, she boasts a long resume of community involvement, as a member of the Clarendon Park Advisory Council and president of the Lakeside Area Neighbors Association, among other groups.n
As is the case in several other races, perhaps the biggest issue in the 46th Ward is affordable housing. Cappleman has come under fire for the eviction of dozens of homeless people from Uptown's "tent city" under the Wilson Avenue viaduct in 2017, and drawn ire from critics who say he has not fought to keep single room occupancy buildings for low-income residents in the ward, or pushed for affordable units as a requirement for new housing developments.
Now seeking his third term in office, Cappleman was previously forced to a runoff election in 2015 and prevailed with 53.7 percent of the vote. The 46th Ward includes parts of the Uptown, Buena Park and Lake View East neighborhoods.
Two candidates with deep ties to Chicago politics advanced to the runoff election in the city's 47th Ward. Matt Martin and Michael Negron earned 39.3 percent and 21.4 percent of the vote, respectively to prevail over seven other candidates running in the 47th Ward - Mayor Rahm Emanuel’s home turf that had no incumbent. The field exploded after outgoing Ald. Ameya Pawar made good on his vow to only serve two terms and is now running for treasurer instead.
Martin is a civil rights lawyer at the Illinois attorney general’s office and serves on a local school council in the area. He also co-founded the Heart of Lincoln Square Neighbors Association, and served on Pawar’s zoning advisory council. Martin's also got the backing of organizations like the Chicago Teachers Union, Service Employees International Union and more, plus several progressive elected officials.
Negron is an attorney and ex-White House staffer for former President Barack Obama. He most recently worked as a policy adviser to Emanuel, touting his work over the last seven years on the city's minimum wage increase, paid sick leave ordinance, investment in affordable housing and more. Negron also served on an area local school council.
The 47th Ward includes parts of the Ravenswood and North Center neighborhoods on the city's North Side.
Contact Us