Movies That Capture Cities Perfectly, Part 1: Chicago

Chicago City

Aaron Sorkin’s drama had us all feeling some type of way, thinking about the long history of Chicago on film. The Trial Of The Chicago 7 was the dramatization of one of American history’s most controversial court cases. But without giving too much away, the dissidence and oppression depicted in the movie resonates deeply with America today. So The Trail Of Chicago 7, got us thinking about other Chicago movies that capture Chicago’s essence like no other.

While there are tons of great Chicago movies, and even though it pains us to exclude movies like Cooley High (1975) and The Fugitive (1993) – here are our favorite movies featuring all that the windy city has to offer.

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Widows (2018)

One of the more recent in this list, and quite essentially one of the ‘most Chicago movies’, stars Viola Davis, Colin Farrell and Liam Neeson in Widows. Steve McQueen’s masterful thriller heist movie brings forward an incredibly insightful script regarding Chicago politics in the late 10’s. Moreover, the director encapsulates the city’s beauty to the movie’s benefit. Additionally, the opening scene of a boat chase in Lake Michigan features a beautiful skyline in the background, and that sets the tone!

The Untouchables (1987)

Adding an Oscar to Brian De Palma’s name, this might be considered an ironic entry on this list. We’re talking about a certain Union Station scene! But what really get’s this on the list is how well it captures the city. From Sean Connery’s famous speech about the Chicago Way to meetings on Michigan Avenue Bridge, this is one of the Chicago movies that takes you all around the city. And you get to visit the Chicago Cultural Center, the Blackstone Hotel, The Chicago Theatre, The City National Bank and Trust Company Building!

Southside With You (2016)

Let’s forget the politics of this movie and just focus on the journey that it takes you on; the delicate and romantic depiction of Barack Obama and Michelle Robinson’s first date. Not only do the actors do a wonderful job, but this is one of the Chicago movies that truly mirrors the city in the 1980’s. Moreover, there’s even a plaque at the Baskin-Robbins at Dorchester and 53rd, which marks the spot where the Obamas shared their first kiss! Dreamy.

Road To Perdition (2002)

Sam Mendes and the master cinematographer Conrad L. Hall beautifully transformed Chicago’s cityscapes into the era of the Great Depression, leading to Hall winning an Oscar. Shot at the famous University Club of Chicago, the Pullman neighborhood, and the suburbs of Geneva and Evanston, this is one of the movies that capture Chicago just perfectly! Additionally, even the interiors shot on set were built in the area.

My Best Friend’s Wedding (1997)

Julianne Porter, portrayed ever so beautifully by true Hollywood gold, Julia Roberts, spends the movie running all over Chicago. Whether it’s driving on Lake Shore Drive or eating at Charlie Trotter’s, she’s there. While some movies that capture Chicago like to use Chicago as a backdrop, P.J. Hogan highlights its beauty in all its glory. From Comiskey Park to Union Station, you could make the dream sight seeing list watching this!

Home Alone (1990)

Few movies do what Home alone did to McCaulay Culkin’s name – that kid was everywhere! The movie was shot mostly in Winnetka, a neighbor of the suburb (Northbrook). And that’s where movie writer John Hugh actually grew up! The northern suburbs are wonderfully captured, as well as the quick trip to a church in Oak Park. It’s tough to think of the holidays and not be reminded of the portrayal of Christmas (and poor forgotten-about Kevin McCallister!) in the Windy City.

The Blues Brothers (1980)

Can this be considered the ultimate Chicago movie? It’s certainly up there. The hit comedy was shot all over the city, covering churches in the South Side to Downtown, you can even find guides to its filming locations online. In fact, some reviews called the movie weird, but the great thing about it is that it all works! Dan Aykroyd and John Buleshi’s odessy takes them all over the city, including sleazy locations like Van Buren flophouse, Maxwell Streed and Wicker Drive.

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Ferris Bueller’s Day Off (1986)

Out of all the John Hughes movies that made it to this list, when you ask for a “Chicago Movie”, all we think of is the day Ferris Bueller skipped school! Ferris and Cameron heckle at Wrigley Field, the gang go to the Art Institute of Chicago, and then there’s the infamous parade sequence. Moreover, Hughes shot the movie almost as if writing a love letter to the city in which he grew up in and it shows.

High Fidelity (2000)

When the time came to adapt Nick Hornby’s hit book into a movie, it was decided that relocation from London to Chicago just made sense. The result? A movie that captures neighborhoods of the city that aren’t often shown on the big screen. Chicagoan John Cusack adds a natural authenticity to scenes shot on Wicker Park, one of the most artistically vibrant neighborhoods in the city at the time of shooting. This film now serves almost as a eulogy to the end of an era in Chicago, giving us glances into the days when people found themselves in record stores.

The Dark Night (2008)

This is one of the movies that capture Chicago very differently, but yet it does. This one’s not particularly set in Chicago. But Christopher Nolan’s beloved Batman movie used the city better than most modern era movies do. It takes full advantage of Lower Wacker Drive. Moreover, one of its best scenes is shot on a famous stretch of Lasalle Street. The overhead shots of Gotham City are beyond fascinating. And a special treat for Chicagoans as Nolan and his team transformed the downtown into something new and vibrant. This movie sets the perfect example for every up and coming filmmaker on how to use a city to the best of its advantage, instead of just using a generic cityscape.

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