After his long-time girlfriend dumps him, a thirty-year-old record store owner seeks to understand why he is unlucky in love while recounting his "top five breakups of all time".
Young Al Capone catches the eye of Johnny Torrio, a criminal visiting New York from Chicago. Torrio invites Capone to move to Illinois to help run his Prohibition-era alcohol sales operation. Capone rises through the ranks of Torrio's gang and eventually takes over. On top, he works to consolidate his power by eliminating his enemies, fixing elections to his advantage and getting rich. In his spare time, Capone courts the principled Iris Crawford.
In 1920s Chicago, Italian immigrant and notorious thug, Antonio 'Tony' Camonte, aka Scarface, shoots his way to the top of the mobs while trying to protect his sister from the criminal life.
In 1992 Chicago, a story of two young legends in their own right begins. As wide-eyed and imaginative best friends Malik and Eric traverse the city, looking to escape the mundaneness of school and the hardships of growing up in public housing, their unbreakable bond is challenged when tragedy shakes their community just as they are learning to fly.
Meet Joel Goodson, an industrious, college-bound 17-year-old and a responsible, trustworthy son. However, when his parents go away and leave him home alone in the wealthy Chicago suburbs with the Porsche at his disposal he quickly decides he has been good for too long and it is time to enjoy himself. After an unfortunate incident with the Porsche Joel must raise some cash, in a risky way.
James “Brick” Davis, a struggling attorney, owes his education to a mobster, but always has refused to get involved with the underworld. When a friend of his is gunned down by a notorious criminal, Brick decides to abandon the exercise of the law and join the Department of Justice to capture the murderer.
Truman Gates, a Chicago cop, sets out to find his brother's killer. Meanwhile, another of his brothers, Briar (a hillbilly) decides to find the killer himself.
A group of ruthless Chicago mob enforcers are sent to Kansas City to settle things with the owner of a slaughterhouse who has taken money that is not his to keep.
Nico Toscani is an Italian immigrant, American patriot, ex-CIA agent, aikido specialist and unorthodox Chicago policeman. He is as committed to his job as he is to his personalized brand of justice—expert and thorough bone-crushing.
The police try to arrest expert hostage negotiator Danny Roman, who insists he's being framed for his partner's murder in what he believes is an elaborate conspiracy. Thinking there's evidence in the Internal Affairs offices that might clear him, he takes everyone in the office hostage and demands that another well-known negotiator be brought in to handle the situation and secretly investigate the conspiracy.
A novice con man teams up with an acknowledged master to avenge the murder of a mutual friend by pulling off the ultimate big con and swindling a fortune from a big-time mobster.
Leonard is an English tailor who used to craft suits on London’s world-famous Savile Row. After a personal tragedy, he’s ended up in Chicago, operating a small tailor shop in a rough part of town where he makes beautiful clothes for the only people around who can afford them: a family of vicious gangsters.
A sociopathic kidnapper methodically pushes a desperate pair of parents to their absolute breaking point.
Julia Reyes, the precocious and strong-willed teenage daughter of first-generation Mexican immigrants, dreams of becoming a famous writer far away from Chicago and her more traditional parents, who wish she were more like her sister Olga, the platonic ideal of a Mexican daughter. However, when Olga is killed in a tragic accident, it is up to Julia to hold her family together. As Julia seeks to break free of her oppressive home, she tries to uncover her sister’s truth, and in the process gains a deep understanding of the wounds her family carries.
A brilliant but socially inept 14-year-old experiences heartbreak for the first time when his two best friends – Cappie, an older-brother figure, and Maggie, the new girl with whom he is in love – fall for each other.
Murderesses Velma Kelly and Roxie Hart find themselves on death row together and fight for the fame that will keep them from the gallows in 1920s Chicago.
Defense attorney Martin Vail takes on jobs for money and prestige rather than any sense of the greater good. His latest case involves an altar boy, accused of brutally murdering the archbishop of Chicago. Vail finds himself up against his ex-pupil and ex-lover, but as the case progresses and the Church's dark secrets are revealed, Vail finds that what appeared a simple case takes on a darker, more dangerous aspect.
Wrongfully convicted of murdering his wife and sentenced to death, Richard Kimble escapes from the law in an attempt to find the real killer and clear his name.
A day in the life of a barbershop on the south side of Chicago. Calvin, who inherited the struggling business from his deceased father, views the shop as nothing but a burden and waste of his time. After selling the shop to a local loan shark, Calvin slowly begins to see his father's vision and legacy and struggles with the notion that he just sold it out.
Tensions rise when the trailblazing Mother of the Blues and her band gather at a Chicago recording studio in 1927. Adapted from August Wilson's play.