Highest-Rated Movies about 'Chicago'

Easy (2016), Bound (1996), A Raisin in the Sun (2008), Pearl Jam: Let's Play Two (2017), Hoop Dreams (1994), The Sting (1973), North by Northwest (1959), Roxie Hart (1942) ... Let's take a look at the ranked list of the best Chicago movies.

#16. 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, crime, classic, violence, chicago, underworld, gunfight ...

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#17. 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: action, thriller, crime, mystery, drama, manhunt, police ...

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#18. 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: comedy, teen, adventure, high school, rebellion, friendship, family ...

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#19. Finding Vivian Maier (2013)

Storyline: Real estate agent John Maloof explains how a trip to a local auction house, in search for old pictures to use for a history book about his neighborhood, resulted in him bidding and winning a box full of old negatives. John goes through the massive quantity of negatives, describes how impressed he is by the quality of the images, becomes quickly determined they are not reverent to his project and just puts them away. That could have very likely had been the end of the story, if the power of the images had not pushed him to fall in love with photography. John confides that his photo hobby quickly motivated him to set up a darkroom and devote large amounts of time printing. As he learned more about photography, he recognized that those negatives he had bought, then stored, were the work of a real master. In an attempt to confirm his suspicion, he selected about 100 images and put them online with the hope that the feedback would confirm his judgement as to the strength of the images.—Lane J. Lubell of Cinemashadow.com

Plot Keywords: documentary, photography, biography, mystery, artist, chicago, new york ...

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#20. Ordinary People (1980)

Storyline: Beth, Calvin, and their son Conrad are living in the aftermath of the death of the other son. Conrad is overcome by grief and misplaced guilt to the extent of a suicide attempt. He is in therapy. Beth had always preferred his brother and is having difficulty being supportive to Conrad. Calvin is trapped between the two trying to hold the family together.

Plot Keywords: family, psychological trauma, depression, father-son relationship, mother-son relationship, grief, guilt ...

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#21. 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: legal drama, courtroom drama, psychological thriller, crime film, mystery, richard gere, murder ...

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#23. 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: comedy, family, christmas, children, adventure, humor, classic ...

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#24. I Am Trying to Break Your Heart (2002)

Storyline: First time director Sam Jones documents the making of Wilco's fourth studio Album, Yankee Hotel Foxtrot. Named after the Wilco song that is featured on Yankee Hotel Foxtrot, an album that strays from the Alt-country that made them famous. Jones' desire was to document the creative work of YHF's production, he seems to have found a bit more, including band members departing and a conflict with Reprise record company. This is a true documentry of art versus money-driven media conglomerates.—J. Robert Putzer <hoplite59@yahoo.com>

Plot Keywords: documentary, music, band, rock, chicago, music industry, creative process ...

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#25. Love Jones (1997)

Storyline: Darius Lovehall is a young black poet in Chicago who starts dating Nina Mosley, a beautiful and talented photographer. While trying to figure out if they've got a "love thing" or are just "kicking it," they hang out with their friend, talking about love and sex. Then Nina tests the strength of Darius' feelings and sets a chain of romantic complications into motion.—Jesse Garon <grifter@primenet.com>

Plot Keywords: romance, love, drama, urban, black culture, chicago, poet ...

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#26. Source Code (2011)

Storyline: Army Captain Colter Stevens finds himself working on a special program where his consciousness can be inserted into another human being. The only catch is can only be there for 8 minutes at any given time. That morning, a bomb exploded on a commuter train just outside Chicago. He occupies the body of teacher going to work on that train and is confused as to what he is doing or why he is there as his last memory is of flying his helicopter on a combat mission in Afghanistan. Those in charge of the program explain to him that there is a bomb on the train, and that he must locate it. More importantly, he must identify the bomber as another bombing is expected later that day. He is also told however that he cannot change the past and can only gather information. As he develops a liking for his traveling companion Christina, he sets out to test that theory.

Plot Keywords: sci-fi, thriller, action, mystery, military, time loop, parallel universe ...

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#27. High Fidelity (2000)

Storyline: Thirty-something Rob Gordon, a former club DJ, owns a not so lucrative used record store in Chicago. He not so much employs Barry and Dick, but rather keeps them around as they showed up at the store one day and never left. All three are vinyl and music snobs, but in different ways. Rob has a penchant for compiling top five lists. The latest of these lists is his top five break-ups, it spurred by the fact that his latest girlfriend, Laura, a lawyer, has just broken up with him. He believed that Laura would be the one who would last, partly as an expectation of where he would be at this stage in his life. Rob admits that there have been a few incidents in their relationship which in and of themselves could be grounds for her to want to break up. To his satisfaction, Laura is not on this top five list. Rob feels a need not only to review the five relationships, which go back as far as middle school when he was twelve, and try to come to terms with why the woman, or girl as the case may ...

Plot Keywords: romance, music, comedy, drama, breakup, coming of age, relationships ...

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#29. Compulsion (1959)

Storyline: In 1924 Chicago, Artie Strauss and Judd Steiner are friends and fellow law students who both come from wealthy backgrounds. They have few true friends as they believe all their contemporaries are intellectually inferior. Within their relationship, Artie is the dominant and Judd the submissive who says he will do whatever Artie tells him. Although Judd acts intellectually arrogant to others, he also shows signs of weakness and reticence most evident to Artie. Part of their goal in life is to experience how it feels to do everything. As such, they plot to commit what they consider the perfect crime - a kidnapping and murder - not only so that they can experience the sense of killing for killing's sake, but also taunt the law with the knowledge of it and their superiority after the fact. They believe their crime is above the law. Their murder of young Paulie Kessler is not so perfect, with evidence at the scene uncovered by one of their law school colleagues, Sid Brooks, who also works for the Globe newspaper. As Artie and Judd try to manipulate their way out of how the evidence may implicate them, their manipulation ultimately backfires and they are charged with the murder. The most famed trial lawyer in town, Jonathan Wilk, is hired to defend the pair despite his atheism being against the families' sensibilities. Jonathan, renowned for his ability to manipulate juries, has to decide how best to defend his clients in the overwhelming face of evidence against them. The testimony of Ruth Evans, Sid's girlfriend, may have some impact on the trial's outcome.—Huggo

Plot Keywords: crime, drama, thriller, courtroom, based on true story, murder, psychological ...

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#30. Thief (1981)

Storyline: Frank is an expert professional safecracker, specializing in high-profile diamond jobs. After having spent many years in prison, he has a very concrete picture of what he wants out of life--including a nice home, a wife, and kids. As soon as he is able to assemble the pieces of this collage, by means of his chosen profession, he intends to retire and become a model citizen. In an effort to accelerate this process, he signs on to take down a huge score for a big-time gangster. Unfortunately, Frank's obsession for his version of the American Dream allows him to overlook his natural wariness and mistrust, when making the deal for his final job. He is thus ensnared and robbed of his freedom, his independence, and, ultimately, his dream.

Plot Keywords: crime, thriller, action, drama, heist, film noir, chicago ...

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