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.

#1. The Weather Underground (2003)

Storyline: When the Beatles land in America in the early 1960s, young men wearing their hair long strike the nation as an abomination. But within a few years, youthful rebellion grows more severe: Witness the Weathermen, the radical antiwar activists who mobilize (unsuccessfully) to overthrow the U.S. government. With contemporary interviews and archival footage, this documentary elucidates the Weather Underground's controversial history and continuing significance.

Plot Keywords: radical, activist, lyndon baines johnson, richard nixon, martin luther king jr., intense, shocking ...

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#5. Hoop Dreams (1994)

Storyline: This documentary follows two young African-Americans through their high school years as they perfect their skills in basketball in the hopes of getting a college scholarship and eventually play in the NBA. Arthur Agee and William Gates both show great potential and are are actively recruited as they look to enter high school. They start off at the same high school but unable to pay an unexpected bill for tuition fees, Arthur has to withdraw and go to the local public high school. The film follows them through their four years of high school and their trials and tribulations: injuries, slumps and the never ending battle to maintain their grades. Through it all, their hoop dreams continue.—garykmcd

Plot Keywords: basketball player, teenager, mother, father, coach, teacher, uplifting ...

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#7. The Sting (1973)

Storyline: Johnny Hooker, a small time grifter, unknowingly steals from Doyle Lonnegan, a big time crime boss, when he pulls a standard street con. Lonnegan demands satisfaction for the insult. After his partner, Luther, is killed, Hooker flees, and seeks the help of Henry Gondorff, one of Luther's contacts, who is a master of the long con. Hooker wants to use Gondorff's expertise to take Lonnegan for an enormous sum of money to even the score, since he admits he "doesn't know enough about killing to kill him." They devise a complicated scheme and amass a talented group of other con artists who want their share of the reparations. The stakes are high in this game, and our heroes must not only deal with Lonnegan's murderous tendencies, but also other side players who want a piece of the action. To win, Hooker and Gondorff will need all their skills...and a fair amount of confidence.

Plot Keywords: con artist, mentor, gangster, amusing, witty, engaging, chicago ...

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#9. Some Like It Hot (1959)

Storyline: When two Chicago musicians, Joe and Jerry, witness the the St. Valentine's Day massacre, they want to get out of town and get away from the gangster responsible, Spats Colombo. They're desperate to get a gig out of town but the only job they know of is in an all-girl band heading to Florida. They show up at the train station as Josephine and Daphne, the replacement saxophone and bass players. They certainly enjoy being around the girls, especially Sugar Kane Kowalczyk who sings and plays the ukulele. Joe in particular sets out to woo her while Jerry/Daphne is wooed by a millionaire, Osgood Fielding III. Mayhem ensues as the two men try to keep their true identities hidden and Spats Colombo and his crew show up for a meeting with several other crime lords.

Plot Keywords: musician, friend, sexy woman, millionaire, mobster, playful, hilarious ...

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#10. I Am a Fugitive from a Chain Gang (1932)

Storyline: Having returned from fighting in World War I, James Allen doesn't want to settle into a humdrum life and decides to set off to find his fortune. He travels the length and breadth of America, working as a skilled tradesman in the construction industry. When times get tough however, he finds himself living in a shelter where an acquaintance suggests they go out for a hamburger. What the friend really has in mind is to rob the diner and Allen soon finds himself working on a chain gang with a long jail sentence. Allen manages to escape however and heads to Chicago where over several years he slowly but surely works his way up the ladder to become one of the most respected construction engineers in the city. His past catches up with him and despite protestations from civic leaders and his many friends in Chicago, he finds himself again on the chain gang. Escaping for a second time, he accepts that to survive, he must lead a life of crime.

Plot Keywords: veteran, prisoner, guard, landlady, lawyer, bleak, brutal ...

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#11. Roxie Hart (1942)

Storyline: In 1927 Chicago, the body of a theatrical agent is found in the apartment of his client, would-be dancer Roxie Hart (Ginger Rogers), who lives with her husband, Amos. Convinced by two reporters that juries never convict pretty women and that she can garner fame by confessing, Roxie, who knows Amos is guilty, agrees. Amos hires snappy lawyer Billy Flynn (Adolphe Menjou) to stir publicity, and Roxie is a sensation. But when public interest flags, Roxie fears she might be convicted after all.

Plot Keywords: dancer, husband, reporter, lawyer, thief, foreman, brash ...

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#13. A Raisin in the Sun (1961)

Storyline: Walter Lee Younger is a young man struggling with his station in life. Sharing a tiny apartment with his wife, son, sister and mother, he seems like an imprisoned man. Until, that is, the family gets an unexpected financial windfall...—Greg Bruno <burlynerd@usa.net>

Plot Keywords: son, mother, wife, widow, sister, suitor, emotional ...

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#15. The Untouchables (1987)

Storyline: After building an empire with bootleg alcohol, legendary crime boss Al Capone rules Chicago with an iron fist. Though Prohibition Agent Eliot Ness attempts to take Capone down, even his best efforts fail due to widespread corruption within the Windy City's police force. Recruiting an elite group of lawmen who won't be swayed by bribes or fear, including Irish-American cop Jimmy Malone, Ness renews his determination to bring Capone to justice.

Plot Keywords: al capone, cop, gangster, accountant, bootlegger, engaging, gutsy ...

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