Chicago has been a playwright’s city for a century, and many of the best plays written here are also about the city itself: its newsrooms and courtrooms, South Side apartments and North Side storefronts, cabs, bleachers and junk shops. This guide collects the essential plays set in Chicago. For each one we explain why the city matters to the story and link every ChicagoCritic review we have published of it, with the producing company, the year and the rating our critic gave.
Our Rule: The Story Has to Happen Here
To make this list, Chicago has to be a setting of the story. Where a play premiered, where its characters come from and where a famous production was staged do not count on their own. Chicago has launched a long list of plays that take place somewhere else, and they belong in a different guide.
We also draw a second line inside the list. In some plays Chicago is essential to the story: the city’s neighborhoods, institutions, politics or history drive what happens, and the play could not be moved without breaking it. In others Chicago is the location: the play is clearly set here and has the feel of the place, but its central conflict could happen in another big American city. Each entry says which kind it is.
Set Primarily in Chicago
Chicago by Maurine Dallas Watkins (1926)
Before Kander and Ebb, there was the play. Maurine Dallas Watkins covered the 1924 murder trials of Beulah Annan and Belva Gaertner for the Chicago Tribune, then turned them into a satire that opened on Broadway at the Music Box Theatre on Dec. 30, 1926. Its Roxie Hart is a Cook County defendant who wins over the jury and the papers with a good lawyer and a better story. Chicago is essential: the play is a send-up of the city’s jails, courts and competing newspapers, written by a reporter who watched them work. It is the source of the 1975 musical.
The Front Page by Ben Hecht and Charles MacArthur (1928)
Hecht and MacArthur were both Chicago newspapermen, and their comedy takes place in the press room of the city’s Criminal Courts Building on the night before an execution, with reporters playing cards, working the phones and fighting over the story. The building at 54 W. Hubbard St. still stands as Courthouse Place, and the City of Chicago’s landmark listing for it names The Front Page. Chicago is essential: the cynical mayor, the sheriff and the cutthroat papers are a portrait of 1920s Chicago journalism and politics.
Our reviews:
- Our review of The Front Page at TimeLine Theatre (2011): Highly Recommended
Native Son, adapted by Nambi E. Kelley from Richard Wright
Richard Wright’s 1940 novel follows Bigger Thomas, a young Black man from the South Side of the 1930s who takes a job as a chauffeur for a wealthy white family and is pulled into a killing. Nambi E. Kelley’s stage adaptation premiered in Chicago in 2014 in a Court Theatre and American Blues Theatre co-production. Chicago is essential: the segregated South Side, its overcrowded housing and the gulf between Bigger’s world and his employers’ are the forces that trap him.
Our reviews:
- Our review of Native Son at Court Theatre with American Blues Theatre (2014): Highly Recommended
A Raisin in the Sun by Lorraine Hansberry (1959)
The Younger family lives in a cramped South Side apartment, and the whole play turns on what they will do with a life-insurance check, above all whether to buy a house in Clybourne Park, a white neighborhood that does not want them. Hansberry drew on her own family’s experience of moving into a white Chicago neighborhood. Chicago is essential: the city’s housing segregation is the plot.
Our reviews:
- Our review of A Raisin in the Sun at TimeLine Theatre (2013): Highly Recommended
Sexual Perversity in Chicago by David Mamet (1974)
Mamet’s early comedy premiered with Chicago’s Organic Theater in 1974 and follows two young men and two young women through the bars, offices, apartments and beaches of single life in the city. The title puts Chicago front and center, but the script keeps the setting loose. Chicago is the location: the dating games and the bluster are recognizably urban and very 1970s, and the city gives them their backdrop rather than their cause. ChicagoCritic has not reviewed a production.
American Buffalo by David Mamet (1975)
Three small-time hustlers plot to steal a coin collection from the back of Don’s Resale Shop, a Chicago junk shop. The play premiered at the Goodman Theatre’s Stage 2 in 1975 and helped announce a new generation of Chicago theater to the rest of the country. Chicago is the location: the shop, the talk and the neighborhood are pure Chicago, but the story of loyalty, greed and botched ambition could play in any city’s back room.
Our reviews:
- Our review of American Buffalo at Steppenwolf Theatre (2009): Recommended
- Our review of American Buffalo by Mary-Arrchie Theatre at Angel Island (2016): Highly Recommended
Bleacher Bums by the Organic Theater Company (1977)
Conceived by Joe Mantegna and created by members of the Organic Theater Company in 1977, Bleacher Bums follows a group of Cubs fans in the Wrigley Field bleachers through one afternoon game, complete with bets, heckling and long-suffering loyalty. Chicago is essential: the play is a love letter to a particular ballpark, a particular team and the particular kind of hope that comes with both.
Our reviews:
- Our review of Bleacher Bums by Open Space Theatre at the Pride Arts Center (2016): Not Recommended
Ma Rainey’s Black Bottom by August Wilson (1984)
Set in a Chicago recording studio in March 1927, this is the only play in August Wilson’s ten-play American Century Cycle that is not set in Pittsburgh. Blues singer Ma Rainey and her band wait out a session for a white producer and manager, and the trumpeter Levee’s anger about who controls, owns and profits from Black music builds to tragedy. Chicago is essential to the story’s world: the city’s 1920s race-record business, with Black artists recording for white-owned companies, is the arena for the conflict, even though the action never leaves the studio.
Our reviews:
- Our review of Ma Rainey’s Black Bottom at Court Theatre (2009): Highly Recommended
Glengarry Glen Ross by David Mamet (1983)
Mamet’s Pulitzer Prize winner takes place in a Chicago real estate office and a nearby Chinese restaurant, where salesmen fight over leads in a contest whose losers will be fired. It is also a good test of our rule: the play premiered at the National Theatre in London in 1983, then had its American premiere at the Goodman Theatre in 1984. What qualifies it is the setting, not the premiere. Chicago is the location: the hustle is vividly local, but the play is about American salesmanship in general. ChicagoCritic has not reviewed a production.
Never the Sinner by John Logan (1985)
John Logan’s first play revisits the 1924 Chicago murder of 14-year-old Bobby Franks by Nathan Leopold and Richard Loeb, two wealthy, academically brilliant young men from the South Side’s Kenwood neighborhood, and the trial that followed. It was first staged in Chicago in 1985. Chicago is essential: it is a true Chicago crime story, tried in the same 1920s court system and newspaper frenzy that produced Chicago and The Front Page.
Our reviews:
- Our review of Never the Sinner at Victory Gardens Theater (2015): Highly Recommended
Pill Hill by Samuel L. Kelley
Six Black friends who start out working in South Side steel mills meet over the years in a basement apartment between 1973 and 1983, measuring who has climbed into professional life and who has not. The title refers to Pill Hill, a South Side neighborhood of doctors and other professionals. Chicago is essential: the steel mills, the South Side and the promise of moving up to Pill Hill frame every argument about success.
Our reviews:
- Our review of Pill Hill at eta Creative Arts Foundation (2009): Not Recommended
Hellcab by Will Kern (1992)
A Chicago cab driver works a Christmas Eve shift, and a stream of passengers, from sweet to drunk to menacing, climbs into the back seat. First produced by Famous Door Theatre in 1992, Hellcab became one of the city’s longest-running holiday shows. Chicago is essential: the cold, the streets and the cross-section of riders make the city the real main character.
Our reviews:
- Our review of Hellcab at Profiles Theatre (2012): Highly Recommended
- Our review of Hellcab at Profiles Theatre’s Main Stage (2013): Highly Recommended
- Our review of the Hellcab remount at Profiles Theatre (2014): Recommended
- Our review of Hellcab at Profiles Theatre (2015): Highly Recommended
Proof by David Auburn (2000)
Auburn, a University of Chicago alumnus, set his Pulitzer Prize winner on the back porch of a house in Hyde Park, near the university. Catherine has spent years caring for her father, a brilliant mathematician whose mind failed him, and must now prove that a groundbreaking proof found in his papers is hers. Chicago is the location, with a strong sense of place: the university neighborhood shapes the characters, but the story of genius, inheritance and doubt is not about the city. ChicagoCritic has not reviewed a production.
Superior Donuts by Tracy Letts (2008)
Arthur Przybyszewski runs a fading donut shop in Uptown that his parents opened, and a young employee with big ideas and bigger debts shakes him out of his rut. Steppenwolf gave the play its world premiere in 2008. Chicago is essential: Uptown’s changing streets and the pressure on an old neighborhood business are the backdrop and much of the subject. One of our critics called it Letts’ ode to Chicago.
Our reviews:
- Our review of Superior Donuts by Mary-Arrchie Theatre (2012): Recommended
- Our review of the Mary-Arrchie Superior Donuts remount at the Royal George (2012): Highly Recommended
Clybourne Park by Bruce Norris (2010)
Norris picks up where A Raisin in the Sun leaves off. Act One takes place in 1959 in the house at 406 Clybourne St. that the Youngers are buying, as the white neighbors try to stop the sale. Act Two returns to the same house in 2009, when the neighborhood is Black and a white couple wants to tear the house down and build bigger. Chicago is essential: the play is about one fictional Chicago neighborhood across 50 years of race, real estate and resentment.
Our reviews:
- Our review of Clybourne Park at Steppenwolf Theatre (2011): Highly Recommended
My Kind of Town by John Conroy (2012)
Investigative journalist John Conroy spent years reporting on the torture of suspects by Chicago police under Cmdr. Jon Burge, and he turned that reporting into this play, which TimeLine Theatre premiered in 2012. Our review called it a truthful drama that puts a human face on police torture in Chicago. Chicago is essential: it dramatizes a real Chicago scandal, and the title’s borrowed civic boast is pointedly ironic.
Our reviews:
- Our review of My Kind of Town at TimeLine Theatre (2012): Highly Recommended
Exit Strategy by Ike Holter (2014)
A crumbling Chicago public high school is scheduled to close at the end of the year, and a handful of teachers, a student and an administrator make a last stand to save it. Jackalope Theatre Company premiered Holter’s play in 2014. Chicago is essential: it grew out of the city’s fights over closing neighborhood schools, and the stakes are a Chicago neighborhood’s. ChicagoCritic has not reviewed a production.
Purpose by Branden Jacobs-Jenkins (2024)
Steppenwolf gave Purpose its world premiere in 2024, and the play went on to win the 2025 Pulitzer Prize for Drama and the 2025 Tony Award for Best Play. It takes place in the South Side home of the Jaspers, a prominent Black political and civil rights family, when a family gathering exposes secrets and rivalries. Chicago is essential: the family’s standing in Chicago politics and its South Side roots are central to what they stand to lose. ChicagoCritic has not reviewed a production.
Ashland Avenue by Lee Kirk (2025)
Pete has run Pete’s TV and Video for more than 40 years and became a local celebrity through his low-budget commercials, but only his first store, on Ashland Avenue, is left. He wants his daughter Sam to take over, and she has other dreams. The Goodman Theatre opened its centennial season with the world premiere in 2025. Chicago is essential: the play is a portrait of a Chicago neighborhood business and a kind of hometown fame only a local TV market can create. ChicagoCritic has not reviewed a production.
Partially Set in Chicago
Chicago Boys by Kathleen Tolan
Set in the 1970s in Chicago and Santiago, Chile, Tolan’s play follows a young American economist, a protégé of University of Chicago professor Milton Friedman, who goes to Chile to promote free-market economics. After the 1973 coup, the military regime turns to the Chilean economists trained at the University of Chicago, the “Chicago Boys,” as killings and disappearances mount. The Goodman staged it in 2011 in its New Stages Amplified series. Chicago is essential to the ideas, since the economics come from Hyde Park, while much of the drama plays out in Chile. ChicagoCritic has not reviewed a production.
Chicago Stories That Aren’t Set in Chicago
The Humans by Stephen Karam feels like a Chicago play to many local theatergoers because it had its world premiere at American Theater Company in 2014 before going on to win the Tony Award for Best Play. But the Blake family is from Scranton, Pa., and the play takes place over one Thanksgiving in a basement duplex in Manhattan’s Chinatown. Under our rule, a Chicago premiere does not make it a Chicago play.
Our reviews:
- Our review of the world premiere of The Humans at American Theater Company (2014): Highly Recommended
More Chicago Plays to Come
Chicago companies keep adding to this list, and we will update this guide as new Chicago-set plays open and as we review new productions of the classics.