25 Movies That Best Capture Chicago

August 6, 2019

If art imitates life, what better way to capture the essence of a city than through its stories and the settings in which those stories are told? Chicago has played a starring role in several Hollywood films from gangster flicks to rom-coms, and from coming-of-age classics to action-packed blockbusters.

Mccormick Place Convention Hall
McCormick Place Convention Hall, on the big screen as The Applied Sciences Division of Wayne Enterprises in The Dark Knight (2008).
Image source: Legendarytrips

Get to know Chicago through its movies before you arrive. Once you get here, explore where the films were shot. We list 25 films that best capture the city and the scenic locations that brought the stories to life:

1. Cooley High (1975)

Cooley High 1975This coming-of-age, high-school drama directed by Michael Schultz offers insight on Chicagoan life in the 1960s. The narrative follows best friends Cochise and Preach as they navigate the highs and lows of the last days of high school. Both protagonists live in the controversial Cabrini-Green housing projects (now demolished), but their adventures take them across Chicago. While most of the locations in the film have been torn down or redeveloped since the 70s (when the film was made), some are still standing and you can visit them even today: The Division Street Bridge (North Branch Canal), the Sedgwick Station (CTA Brown Line), and the Burr Oak Cemetry (Alsip) are all featured in Cooley High. We recommend visiting the Division Street Bridge while you still can, as it’s on the city’s list for redevelopment projects and might not be around for much longer.

2. The Blues Brothers (1980)

The Blues Brothers 1980“Chicago is one of the stars of the movie,” said Dan Aykroyd who stars in the John Landis cult classic. The film’s locations include Maxwell Street (the birthplace of the Chicago Blues), the Pilgrim Baptist Church of South Chicago, and the 95th Street Bridge which acquired fame as the bridge that the Blues Brothers jumped while it was raised. The bridge is located next to the Calumet Fisheries smokehouse (the late Anthony Bourdain was a fan) that served the cast and crew for three days during the shoot and still dishes out delicious fare in case you want to grab a bite at the same place as the Blues Brothers.

3. Thief (1981)

Thief 1981Chicago-born Michael Mann’s neo-noir gangster drama stars James Caan as Frank, an ex-convict who is determined to lead a normal life and desires a wife and family. The film received mixed reviews, but its portrayal of Chicago’s seedy underbelly was on point. Two must-visit locations from the film are Halligan Bar and the Greenmill Cocktail Lounge. The former is located in Lincoln Park and has been around since the prohibition era — it remains a favorite among locals. The Greenmill Cocktail Lounge is a historical bar in Edgewater — it was Al Capone’s favorite place, and he used it to illegally sell liquor during prohibition. (Ask to see the escape doors).

4. Risky Business (1983)

Risky Business 1983It’s the movie that made Tom Cruise and dancing at home in your underwear famous. The film was shot in Chicago’s affluent North Shore areas where writer-director Paul Brickman grew up. He used satire to showcase the lives of 1980s rich Americans — themes include capitalism and the loss of innocence. The Belmont Harbor, The Drake Hotel, and Lake Michigan play prominent parts in the movie.

5. About Last Night (1986)

About Last Night 1986Based on Chicago’s David Mamet’s play, Sexual Perversity in Chicago, the movie explores the lives of promiscuous 20-year-olds trying to find love. Director Edward Zwick shot the film in locations like The Original Mother’s and Kelly’s Pub, both are still in business today. Exterior shots of the city show Wells Street Bridge, Grant Park, and Wrigley Field (home to the Chicago Cubs).

6. The Untouchables (1987)

The Untouchables 1987While there have been several gangster films based in Chicago, director Brian De Palma’s The Untouchables remains the quintessential mob movie. Written by David Mamet, it stars Hollywood legends like Sean Connery (who won an Academy Award for his role as Jim Malone), Robert De Niro, and Kevin Costner. This stellar cast acted their parts in iconic Chicago landmarks like the Chicago Theatre, The Rookery Building, Michigan Avenue Bridge, Our Lady Of Sorrow Basilica and Al Capone’s residence, The Lexington Hotel (now demolished).

7. Backdraft (1991)

Backdraft 1991The Ron Howard directed thriller put the spotlight on two Chicago firefighters who follow the trail of a serial arsonist. The film was nominated for three academy awards and featured the Graceland Cemetry — which is the resting place of Chicago greats like Mies van der Rohe, and the inventor of the sleeping car, George Pullman. The fire stations featured in the film are the Fire Station at 3002 W. 42nd Street and the Chinatown Firestation on Cermak Road. Our must-visit recommendation from the movie is the Uptown Theatre. This stunning piece of architecture will be renovated soon so go have a look while you still can.

8. The Fugitive (1993)

The Fugitive 1993Don’t limit your trip to downtown Chicago and the northern suburbs. The South Side has a lot to offer too. Andrew Davis directed most of the film in Chicago’s non-touristy South Side. The area has some of the city’s best architecture, parks, restaurants, and academic institutions, so go off the beaten path and discover what’s south of the Loop. Our suggestions? A visit to Frank Lloyd Wright’s Robie House, a meal at Hyde Park’s Valois Restaurant (President Obama’s favorite), and a walk in the magnificent campus of the University of Chicago. If you want to stick to strictly movie locales: The Chicago Hilton and the historical Cook County Hospital (currently under renovation) were both in The Fugitive.

9. Hoop Dreams (1994)

Hoop Dreams 1994This is the only documentary on our list because Chicagoan Steve James has captured the city better than most fictional movies. It follows two aspiring basketball players from low-income families as they struggle to get scholarships at colleges of their choice. Most of the locations in the documentary have been demolished and redeveloped except the University of Illinois at Urbana-Champaign — the documentary was filmed on their campus located 2 hours from Chicago.

10. While You Were Sleeping (1995)

While You Were Sleeping 1995The things we do for love! Like pretending to be the fiancée of a man (who’s in a coma) you have a secret crush on only to fall in love with his brother. Sandra Bullock plays a CTA token collector at Chicago’s Randolph/Wabash Station (now closed). Directed by Jon Turteltaub, the film stars Bullock, Bill Pullman, as well as Chicago’s Emmanuel Episcopal Church (in La Grange which was the suburb where Pullman’s character’s family lived), Our Lady of Mount Carmel Church, and Northwestern Memorial Hospital.

11. My Best Friend’s Wedding (1997)

My Best Friend’s Wedding 1997Is there anything more heart wrenching than unrequited love? Julia Roberts’ character races from New York to Chicago to win back her ‘best friend’ from the Chicagoan (Cameron Diaz) who stole his heart. P. J. Hogan directed the rom-com which features O’Hare Airport, the US Cellular Field which is now called the Guaranteed Rate Field, the Fourth Presbyterian Church , the Cuneo Mansion and Gardens, and Union Station.

12. Chicago Cab (1997)

Chicago Cab 1997Directed by husband-wife duo Mary Cybulski and John Tintori, the film is based on the play Hellcab by Will Kern. Chicago-born Paul Dillon plays the title role and is supported by a cast of Chicagoan actors including John Cusack, John C. Reilly, and Gillian Anderson. Known simply as the ‘cab driver,’ Dillon’s character takes passengers across Chicago’s North Side, Loop, South Side, and O’Hare. He picks up passengers from the InterContinental Hotel, the Park View Diner, and Rogers Park — they’re all dealing with existential crises and make the cabbie their confidant.

13. High Fidelity (2000)

High Fidelity 2000Remember the time when we made mixtapes for our crushes? We miss those days, and if you do too, watch High Fidelity. It’s the story of an indie-music-loving, record store owner, played by Chicago’s John Cusack, reminiscing about lost loves. Director Stephen Frears filmed the modern love story in some of Chicago’s most popular venues for indie acts like the Schubas Tavern, the Music Box Theater, and the Biograph Theater.

14. Return to Me (2000)

Return To Me 2000This is for David Duchovny fans who loved the X-Files but long to see Agent Mulder in a romantic avatar. In Return to Me, Duchovny’s character is grieving the death of his wife. He falls in love with a waitress/artist (Minnie Driver) who happens to receive said wife’s heart in a transplant. The film’s director, Bonnie Hunt, is a Chicago local and a longtime customer at the famous (it was Frank Sinatra’s favorite) Twin Anchors Restaurant and Tavern (called O’Reilly’s in the film), which is where Driver’s character works. Also seen in the film is the Buckingham Fountain (one of the largest in the world) in Grant Park.

15. The Weather Man (2005)

The Weather Man 2005Filmmakers love filming in sunny Chicago which is why we put Gore Verbinski’s Weather Man on the list — it features a Chicago winter! Nicolas Cage stars in the title role of a frustrated and disillusioned weatherman who’s having a midlife crisis. Every winter, Chicago turns into an icy wonderland and this film showcases some of the city’s prettiest winter locales like a partially frozen Lake Michigan and ice skating in Millennium Park. Cage’s character takes up archery as a distraction from his quotidian problems — he pursues his new hobby at the Glisson Archery Range and Pro Shop.

16. The Dark Knight (2008)

The Dark Knight 2008Chicago is Gotham city in what we think is Christopher Nolan’s best work yet, and some of it was filmed right here at McCormick Place — the Convention Hall of the West Building plays the role of the Applied Sciences Division of Wayne Enterprises, while the Richard J. Daley Center became the headquarters of Wayne Enterprises. Fun fact: the Daley Center was Chicago’s first skyscraper to be built in a modern rather than classical style, and the Chicago Picasso, the 50-foot sculpture that the famous artist gifted to Chicago, was commissioned for the building. The final work of architect Mies Van der Roh, the IBM Building at 330 North Wabash, was used to film the offices of Harvey Dent, the mayor, and the police commissioner, and another iconic Chicago landmark, The Berghoff restaurant, is where Lt. Gordon arrests mob boss Maroni. And, what Batman movie is complete without a shot of him scanning the city perched on its highest tower? In The Dark Knight, Batman surveys Gotham from the Willis Tower (formerly Sears Tower).

For Heath Ledger Fans: (Because who isn’t?) Ledger’s Oscar-winning (he also won the BAFTA, a Golden Globe, and the Screen Actors Guild Award for this role) Joker robs the Gotham National Bank at the start of the film — the Old Chicago Post Office portrayed the role of the bank. Batman and Joker first face-off against each other at South LaSalle Street, you can see the Chicago Board of Trade Building at the end of the street, and the final fight at the end of the film shows the exterior of the Trump Tower, which was under construction during filming.

17. Drinking Buddies (2013)

Drinking Buddies 2013Chicago-based director Joe Swanberg captures the city through non-touristy locations that only true locals recognize. So if you want to ditch The Dark Knight fan craze and experience Chicago like a local, visit the locations featured in Drinking Buddies. The film’s protagonists work at Revolution Brewing, (an actual brewery in Logan Square), and actress Olivia Wilde’s character and her friends are seen playing pool at a real-life, indie music venue, The Empty Bottle.

18. Southside With You (2016)

Southside With You 2016The biographical romantic written and directed by Richard Tanne tells the story of America’s first African American President, Barack Obama, and the love of his life Michelle Robinson’s first date in Chicago. The on-screen couple visits the Chicago Cultural Center, they walk through Douglas Park, and kiss on a bench outside Baskin-Robbins. The movie doesn’t feature the actual ice cream store where the kiss happened but the spot where the real-life kiss took place has been commemorated with a plaque. So if you want to kiss your beloved at the same spot, visit Dorchester Avenue and 53rd Street in Chicago’s Hyde Park.

19. Widows (2018)

Widows 2018The critically-acclaimed heist movie directed by Steve McQueen stars the superior acting talent of Viola Davis, Colin Farrell, and Liam Neeson. It deals with classic Chicago themes like racial inequality, corrupt politicians, the mob, and people with an indomitable spirit that the Windy City is known for. This movie is the latest one on this list so a lot of its locations haven’t been torn down or redeveloped which means you really can experience the Chicago seen in the film. We highly recommend a visit to Daley’s restaurant, it’s featured in the film and is one of Chicago’s oldest eateries (since 1892). Also spotted in the film is the Waldorf Astoria on the Gold Coast and the non-touristy Parkway Gardens.

20. Call Northside 777 (1948)

Call Northside 777 1948This was the first movie ever to be shot on location in Chicago. Directed by Henry Hathaway, the film noir was based on the real-life story of a Chicago cop’s murder and the men who were wrongly convicted for the act. The Chicago of today looks nothing like what it did in 1948, except for its most historic landmarks that are still standing proud like the great Wrigley Building, and the Art Deco masterpiece, Merchandise Mart. Both buildings made their Hollywood debut in Call Northside 777.

21-25 SPECIAL MENTION: JOHN HUGHES

A list of Chicago movies is not complete without paying homage to filmmaker John Hughes. He wasn’t born a Chicagoan but made the city his adopted home, and filmed most of his movies here. Hughes lived in the sheltered suburb of Northbrook and he attended Glenbrook North High School, which was featured in his most famous work, Ferris Bueller’s Day Off (1986). Most of Hughes’s films in the 1980s like Sixteen Candles (1984), The Breakfast Club (1985), and Uncle Buck (1989) were coming-of-age, melancholic comedies. All these films were shot in Chicago’s affluent northern suburbs, so if you want to make a day out of visiting only John Hughes film locales, head to Highland Park, Glencoe Union Church, Glencoe Beach, Emmit’s Irish Pub, and it’s not in the suburbs, but it was seen in Ferris Bueller’s Day Off, The Art Institute of Chicago.

The last film on this list is Hughes’s Baby’s Day Out (1994), in which said baby outsmarts its kidnappers and crawls across downtown Chicago. Iconic locations include the Lincoln Park Cultural Center and the Lincoln Park Zoo.

Baby's Day Out 1994

By now you have probably short-listed the locations you want to explore. The next thing to do is read our blog on the best apps for getting around Chicago, and start discovering the city one movie at a time!

Share

The above article was written for this Chicago blog hosted by the Carlton Inn MidwayMidway Airport’s Best Value Hotel. The blog is meant to educate and entertain. Management does not warrant the accuracy or completeness of the information on this website. Carlton Inn Midway may make changes to the content or policies at any time without prior notice. That which was written above does not represent the voice of hotel management. Rather, it is the lone voice of the writer.