Highest-Rated Movies about 'Chicago', Sort by Popularity

The Weather Underground (2003), Henry: Portrait of a Serial Killer (1986), A Raisin in the Sun (2008), The Stratton Story (1949), Hoop Dreams (1994), Carrie (1952), The Sting (1973), It Happens Every Spring (1949) ... Let's take a look at the ranked list of the best Chicago movies.

#16. Days of Heaven (1978)

Storyline: Bill and Abby, a young couple who to the outside world pretend to be brother and sister are living and working in Chicago at the beginning of the century. They want to escape the poverty and hard labor of the city and travel south. Together with the girl Linda (who acts as the narrator in the movie) they find employment on a farm in the Texas panhandle. When the harvest is over the young, rich and handsome farmer invites them to stay because he has fallen in love with Abby. When Bill and Abby discover that the farmer is seriously ill and has only got a year left to live they decide that Abby will accept his wedding proposal in order to make some benefit out of the situation. When the expected death fails to come, jealousy and impatience are slowly setting in and accidents become eventually inevitable.

Plot Keywords: worker, sister, girlfriend, farmer, wealthy man, sad, emotional ...

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#17. Anita O'Day: The Life of a Jazz Singer (2007)

Storyline: A documentary look at the improvised life of Anita O'Day (1919-2006), singer and stylist whose timing, phrasing, interpretations, and unique sound put her among the finest vocalists of jazz. Interviews with her late in life are interspersed with archival footage of performances and old interviews as well as with comments by friends, arrangers, critics, and other musicians. She talks about singing without a uvula (sing eighth notes), of jail time for a marijuana arrest, of taking and kicking heroin, of finally making money after appearing at the Newport Jazz Festival, of loss, of a broken arm that almost cost her life, and of living in 4/4 time, one day at a time, smiling.—<jhailey@hotmail.com>

Plot Keywords: jazz singer, friend, critic, musician, inspiring, engaging, chicago ...

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#18. Indestructible (2007)

Storyline: A monastery high atop the mountains of northwest China ... the living room of a family confronted with terminal illness ... the office of renowned neurologist Oliver Sacks ... the Wailing Wall of Jerusalem... Indestructible portrays an epic journey of self-discovery for filmmaker and single father Ben Byer as he battles the incurable and fatal neuro-degenerative disease, ALS. A cinematic adventure filled with extraordinary characters and breathtaking landscapes, beautifully shot by Academy Award nominee Roko Belic (Genghis Blues), Byer takes a visually stunning global quest to survive as he begins to understand the power of the human condition. An extraordinary self-portrait of a man confronted with life's ultimate challenge, Indestructible goes deep within the human experience for a fascinating, funny and inspiring story of the conflict between hope and fate.—ALS Film Fund

Plot Keywords: sick person, doctor, inspiring, emotional, sad, moving, china ...

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#19. Down in the Delta (1998)

Storyline: Sinclair family matriarch Rosa Lynn (Mary Alice) raises enough money to help her two grandchildren and drug-addicted adult daughter, Loretta (Alfre Woodard), move to a small Mississippi town in order to escape the dangers of inner-city Chicago. There, Loretta and her kids are taken in by her gruff uncle, Earl (Al Freeman Jr.), who attempts to instill a work ethic and sense of history in his niece. With the help of Earl's tough love, Loretta does her best to put her past demons behind her.

Plot Keywords: single mother, grandmother, uncle, wife, son, daughter, touching ...

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#20. The Fugitive (1993)

Storyline: A well respected Chicago surgeon Dr. Richard Kimble has found out that his wife, Helen, has been murdered ferociously in her own home. The police found Kimble and accused him of the murder. Then, Kimble (without Justifiable Reason) was tried, convicted, and sentenced to death. However, on the way to prison, Kimble's transport crashed. Kimble escapes and is now on the run. Deputy Samuel Gerard from Chicago takes charge of the chase of Kimble. Meanwhile, Kimble takes up his own investigation to find who really killed his wife, and to lure Gerard and his team into it as well.

Plot Keywords: surgeon, marshal, widower, wife, gripping, thrilling, suspenseful ...

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#21. Ferris Bueller's Day Off (1986)

Storyline: High school student Ferris Bueller wants a day off from school and he's developed an incredibly sophisticated plan to pull it off. He talks his friend Cameron into taking his father's prized Ferrari and with his girlfriend Sloane head into Chicago for the day. While they are taking in what the city has to offer school principal Ed Rooney is convinced that Ferris is, not for the first time, playing hooky for the day and is hell bent to catch him out. Ferris has anticipated that, much to Rooney's chagrin.

Plot Keywords: teenager, best friend, girlfriend, principal, sister, amusing, charming ...

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#22. Scarface (1932)

Storyline: Johnny Lovo rises to the head of the bootlegging crime syndicate on the south side of Chicago following the murder of former head, Big Louis Costillo. Johnny contracted Big Louis' bodyguard, Tony Camonte, to make the hit on his boss. Tony becomes Johnny's second in command, and is not averse to killing anyone who gets in his and Johnny's way. As Tony is thinking bigger than Johnny and is not afraid of anyone or anything, Tony increasingly makes decisions on his own instead of following Johnny's orders, especially in not treading on the north side run by an Irish gang led by a man named O'Hara, of whom Johnny is afraid. Tony's murder spree increases, he taking out anyone who stands in his and Johnny's way of absolute control on the south side, and in Tony's view absolute control of the entire city. Tony's actions place an unspoken strain between Tony and Johnny to the point of the two knowing that they can't exist in their idealized world with the other. Tony's ultimate downfall may be one of two women in his life: Poppy, Johnny's girlfriend to who Tony is attracted; and Tony's eighteen year old sister, Cesca, who is self-professed to be older mentally than her years much to Tony's chagrin, he who will do anything to protect her innocence. Cesca ultimately comes to the realization that she is a lot more similar to her brother than she first imagined.—Huggo

Plot Keywords: gangster, sister, criminal, fiery, frenetic, gripping, thrilling ...

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#23. Night Is My Future (1947)

Storyline: The ambitious Stanton "Stan" Carlisle works in a sideshow as carny and assistant of the mentalist Zeena Krumbein, who is married with the alcoholic Pete. The couple had developed a secret code to pretend to read minds and was successful in the show business before Pete starts drinking. Stan stays with them expecting to learn their code and leave the carnival to be a successful mentalist. Stan also flirts with the gorgeous Molly that lives in the carnival with the strong Bruno. Zeena and The Savage, an alcoholic man that eats live chickens that the audiences believe that is a savage, are the greatest attractions of the sideshow. When Stan gives booze to Pete and he dies, Stan finds that Pete had drunk methyl alcohol and not his booze, but he feels guilty for the death of him. Zeena teaches the code to him and Molly helps Stan to learn them. After an incident, Stan is forced to marry Molly and he decides to move to Chicago with her to become a sensation in a night club. One day, he meets the psychologist Lilith Ritter and he finds that she tapes the sessions with her clients from the high-society. The trickster Stan envisions a scheme to raise a high amount of money swindling rich people. But his ambition brings him back to the life in the sideshow.—Claudio Carvalho, Rio de Janeiro, Brazil

Plot Keywords: geek, mind reader, psychiatrist, strong man, con artist, dark, incredible ...

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#24. Brat 2 (2000)

Storyline: Danila Bagrov meets his army buddy Konstantin Gromov in Moscow, with whom he fought in Chechnya. The friend tells Danila about his twin brother Dmitry, who is a professional hockey player in America. However, the team owner, in cahoots with his Russian partner, has swindled the young star into an oppressive contract, allowing them to rob him blind. Several days after this conversation, Danila finds Konstantin dead. In order to straighten things out and avenge his friend, Danila goes to Chicago.

Plot Keywords: friend, young man, brother, hockey player, thrilling, tense, rousing ...

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#25. Road to Perdition (2002)

Storyline: 1931. Mike Sullivan and Connor Rooney are two henchmen of elderly downstate IL-based (Quad City area, though much of the action takes place in the Chicago area) Irish-American mobster John Rooney, Connor's father. In many respects, John treats Mike more as his son, who he raised as his own after Mike was orphaned, than the volatile Connor, who nonetheless sees himself as the heir apparent to the family business. One evening, Mike's eldest son, twelve year old Michael Sullivan Jr., who has no idea what his father does for a living, witnesses Connor and his father gun down an associate and his men, the situation gone wrong initiated from an action by Connor. Caught witnessing the incident, Michael is sworn to secrecy about what he saw. Regardless, Connor, not wanting any loose ends, makes an attempt to kill Mike, his wife and their two sons. Mike and the surviving members of his family know that they need to go on the run as Connor, who has gone into hiding, will be protected through ...

Plot Keywords: hit man, mobster, son, psychopath, father, dark, suspenseful ...

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#26. The Narrow Margin (1952)

Storyline: When a mobster's widow decides to testify and provide names of others involved in evil deeds, she goes undercover to avoid being killed. Onboard a train going cross-country, she's being escorted in order to testify. Cop Walter Brown and his partner are assigned the task, but the mob are on their trail, attempting to make sure she never reaches her destination.—Col Needham <col@imdb.com>

Plot Keywords: widow, gangster, partner, police officer, detective, suspenseful, train ...

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#27. The Public Enemy (1931)

Storyline: Tom Powers and Matt Doyle are best friends and fellow gangsters, their lives frowned upon by Tom's straight laced brother, Mike, and Matt's straight laced sister, Molly. From their teen-aged years into young adulthood, Tom and Matt have an increasingly lucrative life, bootlegging during the Prohibition era. But Tom in particular becomes more and more brazen in what he is willing to do, and becomes more obstinate and violent against those who either disagree with him or cross him. When one of their colleagues dies in a freak accident, a rival bootlegging faction senses weakness among Tom and Matt's gang, which is led by Paddy Ryan. A gang war ensues, resulting in Paddy suggesting that Tom and Matt lay low. But because of Tom's basic nature, he decides instead to take matters into his own hands.

Plot Keywords: gangster, bootlegger, police officer, veteran, friend, melodramatic, brash ...

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#28. The Best Man (1999)

Storyline: After writing a soon-to-be bestselling novel, writer and committed bachelor Harper Stewart (Taye Diggs) attempts to hide the fact that his saucy new book is loosely based on the lives and loves of his tight-knit group of friends. Harper is set to be best man at his friend Lance's (Morris Chestnut) wedding, and all his friends will be in attendance. When an advance copy of the book makes its way into the hands of his ex-flame, Jordan Armstrong (Nia Long), Harper attempts to keep it under wraps.

Plot Keywords: writer, groom, bride, ex-girlfriend, friend, confident, playful ...

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#29. Primal Fear (1996)

Storyline: When a young man, Aaron, is charged with the horrific murder of Archbishop Rushman, hot-shot Chicago lawyer Martin Vail takes on his defense at no charge. Aaron was a homeless street kid before he was taken in by the Archbishop. He's shy and speaks with a stammer. Vail is convinced that Aaron is innocent but after discovering a video that shows Aaron may have had good reason to want the Archbishop dead, he begins to question that conclusion. When Aaron lashes out at the psychologist examining him another personality, Roy, is revealed. With the trial already underway, Vail cannot change Aaron plea and so has to find a way to introduce his client's condition. Aaron has something of a surprise for him as well.

Plot Keywords: attorney, altar boy, priest, psychiatrist, prisoner, suspenseful, gripping ...

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#30. Home Alone (1990)

Storyline: It is Christmas time and the McCallister family is preparing for a vacation in Paris, France. But the youngest in the family named Kevin got into a scuffle with his older brother Buzz and was sent to his room which is on the third floor of his house. Then, the next morning, while the rest of the family was in a rush to make it to the airport on time, they completely forgot about Kevin who now has the house all to himself. Being home alone was fun for Kevin, having a pizza all to himself, jumping on his parents' bed, and making a mess. Then, Kevin discovers about two burglars, Harry and Marv, about to rob his house on Christmas Eve. Kevin acts quickly by wiring his own house with makeshift booby traps to stop the burglars and to bring them to justice.

Plot Keywords: boy, mother, old man, con artist, brother, hilarious, heartwarming ...

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