The 10 Best Chicago-Based Movies, Ranked According To IMDb

The Amazon Prime Video exclusive series Night Sky is a riveting and emotional journey through space, but some are conflicted over the season 2 setup and think it should have stayed as a limited series. The show has a unique take on space exploration, as an elderly couple’s shed holds a door to distant galaxies, but when they aren’t walking through that door, the couple is living in the Windy City.

Chicago has been a city that filmmakers love to shoot in, and it’s one of those cities that becomes a character itself, just like New York or Los Angeles. Several Christmas films take place there, as do many coming-of-age flicks and mob movies, and the movies’ setting is part of what makes them great. Between movies released during the Prohibition and modern movies set during the Prohibition, there’s so much history when it comes to Chicago in film.


10 Scarface (1932) – 7.7

1983’s Scarface is one of the most iconic movies ever, but many people don’t know that the Miami-based movie is actually a remake of a much older film from 1932. The original movie is a way more by-the-numbers mob movie, as it isn’t about immigrants or the American dream, and it isn’t even set in Miami. And as it’s pre-Coda, meaning it was made before censorship guidelines were implemented, it’s excessively violent too.

The film is about a Chicago gangster who rises through the ranks of the city’s gangland, and the location is as tied to the movie just as Miami is to the remake. Surprisingly, even though the 1983 movie is so iconic, another Scarface remake is in development, and it’ll be interesting to see if it goes back to the series’ roots or takes place in another entirely different but distinct American location.

9 Glengarry Glen Ross (1992) – 7.7

Glengarry Glen Ross turned 30 this year, but the movie is still as relevant today as it has ever been, as it depicts the inherent stress and constant worry salespeople have about losing their jobs. The movie has an unbelievable all-star cast that includes Al Pacino, Jack Lemmon, Ed Harris, Alan Arkin, and so many others who play unnerved salesmen. Not only that but the “ABC” speech is still referred to in sales to this day.

Chicago isn’t necessarily on full display in the 1992 movie, as most of the scenes are in places like bars and offices, which makes sense given that it’s based on the stage play of the same name. However, the exaggerated amount of rain is evidence enough that the movie is set in the Windy City.

8 Road To Perdition (2002) – 7.7

Road to Perdition is influenced by a 1930s Chicago gangland, but it isn’t based on any true story or real-life mobster. Instead, it follows an original character and tells a wonderful story while depicting what it was like living in the period. The movie follows a gangster and his son who seek revenge on the ones who murdered their family, and it’s one of the best non-superhero comic book movies ever.

Like Glengarry Glen Ross there’s so much rain in Road to Perdition, but the rain is just one part of what makes the visually stunning movie what it is. Road to Perdition wonderfully showcases the fashion of the Great Depression-era Chicago, and the production design of the buildings and the vehicles of the era is so impressive too.

7 Home Alone (1970) – 7.7

Home Alone is one of many John Hughes movies that take place in Chicago. The beloved filmmaker always made great use of his hometown, and he always made sure to make it look incredible. Whether it’s Sixteen Candles, Weird Science, or Planes, Trains, and Automobiles, the director created some of the most entertaining

’80s films, but Home Alone is the most classic of the lot.

The movie is an annual staple over the holiday season, and though it doesn’t show off the landmarks of Chicago like the sequel does with New York, it perfectly captures what it’s like living in the suburbs of the city, especially over Christmastime. However, some audiences think it Home Alone would be better if it was R-rated, which makes sense given that Kevin definitely has the makings of a serial killer.

6 The Fugitive (1993) – 7.8

The Fugitive is one of the most iconic Chicago-based movies because its location is so imperative to the plot. The film is a cat-and-mouse chase thriller that sees a U.S. Marshal trying to smoke out a doctor, Richard Kimble, who is wanted for the murder of his wife.

Chicago is like the playground where the Marshal is trying to find Kimble, and L-trains, Union Station, and so many other landmarks play an important part in the 1993 film. Even Kimble’s apartment is a famous Chicago location, and it was recently on sale for $4 million. Even in the almost 30 years since its release, few cat-and-mouse movies have reached the quality of the 1993 release, not even its far inferior sequel, U.S. Marshal.

5 The Breakfast Club (1985) – 7.8

The Breakfast Club sees John Hughes at the peak of his career, as he was effortlessly throwing out one classic coming-of-age movie after another. The 1985 movie is about a group of very different midwestern kids who all have weekend detention. They all grow closer — the jock and the emo, the popular girl and the townie — and unite to take on the evil principle.

But while the film is great, it doesn’t exactly make audiences want to book a trip to the Windy City, and most would never even know that it’s set in Chicago. The Breakfast Club might be set in Chicago, but not much of it is seen, as almost the entirety of the movie takes place in the school.

4 Ferris Bueller’s Day Off (1986) – 7.8

Ferris Bueller’s Day Off is yet another Chicago-based movie written and directed by John Hughes, but while both Home Alone and The Breakfast Club are fairly isolated and mostly take place in one location, the 1986 movie is exactly the opposite. It could even be considered a 100-minute advertisement to get viewers to visit the city.

The film shows the Von Steuben Day Parade in great detail, the characters attend a Chicago Cubs baseball game, and they visit the top of the 108-story Willis Tower. Not only that, but one of the most popular lines in the movie is “The sausage king of Chicago.” Chicago’s role in the release is what makes it John Hughes’ best comedy.

3 The Blues Brothers (1980) – 7.9

While it’s a pretty niche subgenre, The Blues Brothers is undoubtedly one of the best musical comedies ever, and with it being based on a Saturday Night Live sketch, a surprising amount of production value went into it too. Not only is the music so much fun, and not only are Dan Aykroyd and John Belushi a hilarious on-screen duo, but it has one of the most epic car chases in cinema history too.

But what makes the movie so soaked in Chicago’s culture and way of life isn’t the landmarks or anything else, but the characters’ vernacular. The hilarious way the main characters deliver the iconic line of the movie in a Chicago accent is what makes it so iconic in the first place, as they declare, “We’re on a mission from Gahd.”

2 The Untouchables (1987) – 7.9

The number of movies about Al Capone, the most notorious Chicago gangster ever, are innumerable, so many have come and gone, but the one that has stood the test of time and is even considered great is 1987’s The Untouchables. The movie tells an important part of Chicago’s history as it’s about Capone and his men supplying liquor to speakeasy bars during Prohibition, but that’s the least criminal thing the mobster does in the film.

Because of its ties to the 1930s and breaking down the Prohibition era, it’s one of the most imperative Chicago-based movies ever. However, though the 1987 release follows real-life prohibition agent Eliot Ness, who attempts to bring down Capone, the film is actually fictionalized, but that’s what makes it so exciting.

1 The Sting (1973) – 8.3

The Sting is unlike any other movie of its kind, as it’s a crime film that’s once again set during the 1930s. However, being a crime caper, it has a completely different tone from all the others. The 1973 release follows two grifters who work together to build a complex con to rob a mob boss for all he’s worth. The film is so much fun and has a rather optimistic vibe despite being set in the thick of the Great Depression.

While sting operations were popular before the movie’s release, it wasn’t until the 1973 film that studios and networks started trying to make entertaining movies and TV shows that featured stings of their own. So many films are about complicated plots to rob money from a mark that doesn’t know they’ve been robbed until long after it happened, but The Sting is the true original, and it remains the best.

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