13 Best Chicago Movies to Add in Your Watchlist

Chicago always had “rivalry” with New York and LA in terms of being the best city. It may come second to the Big Apple hence the moniker “The Second City”. However, it has its fair share of incredible landmarks and fascinating buildings. These attractions, plus the bustling neighborhoods, have become locations for memorable movies.

We’ve searched the internet for the 13 Best Chicago Movies celebrating the breathtaking aesthetic of the city’s landscapes. They also show the inner streets and the soul of the Windy City. We’ve also asked Chicagoans to share movies that highlight the spirit of their hometown.

So, get ready to be transported to old and new Chicago. Travel back in time or revel at the present as we present the best this city has to offer.

1. Chicago (2002)

English, Hungarian 1h 53m IMDb
Chicago (2002) Best Chicago Movies to Add in Your Watchlist

Rob Marshall

Stars: Renée Zellweger, Catherine Zeta-Jones, Richard Gere

This 2002 Academy Award best picture has “all that jazz”. You can attribute it to the mesmerizing mix of music, dance scenes, comedy, drama, and a star-studded cast.

The award-winning lead stars Renee Zellweger and Catherine Zeta-Jones brought the movie to another level- the ladies gave a rousing performance as actors and singers. Loosely based on a true story, it follows two women murderers who face death row simultaneously.

Zeta-Jones gave a superb performance in this musical, winning her an Oscar for best supporting actress. Even the male leads, such as Richard Gere and John C. Reilly, complemented the ladies’ energies.

2. The Trial of the Chicago 7 (2020)

English, Latin, French 2h 9m IMDb
The Trial of the Chicago 7 (2020) Best Chicago Movies to Add in Your Watchlist

Aaron Sorkin

Stars: Eddie Redmayne, Alex Sharp, Sacha Baron Cohen

The film tells the story of seven student activists and militant yippies whose protests led to violent confrontations and run-ins with the police. The federal government charged them with conspiracy and other charges in response to these riots.

The movie is a brave telling of the unfair judiciary system. It reveals the challenges brought about by the Vietnam War and how it affected so many people.

One of the chants in the movie, “the world is watching,” will haunt you until the end. It speaks volumes about how one injustice can spark a revolution.

3. Beats (2019)

English 1h 49m IMDb
Beats (2019) Best Chicago Movies to Add in Your Watchlist

Chris Robinson

Stars: Khalil Everage, Evan J. Simpson, Ashley Jackson

Beats is an inspiring film about a teenage music prodigy living in a Chicago suburb. He is isolating himself from the world due to past traumas.

Until one day, a school security guard forges a friendship with him. It so happens that he is also a struggling music producer raring to redeem his career. The unlikely friends bonded over their love for hip-hop music and creating unique beats.

Dubbed an ode to Chicago’s southside, it reveals how violence, fear, and hardship shape a person. The camera work, editing, and music are excellent. It’s a great watch, especially with your teen kids.

4. The Big Sick ( 2017)

English, Urdu 2h IMDb
The Big Sick ( 2017) Best Chicago Movies to Add in Your Watchlist

Michael Showalter

Stars: Kumail Nanjiani, Zoe Kazan, Holly Hunter

Director and producer Judd Apatow is known for his raunchy films. However, it seemed that he created a romcom gem with this film. It starts when Kumail, a Pakistani, and Emily, an American, fall in love.

Things became challenging when their cultures began to clash. It introduces new cultural perspectives on love, relationships, and marriage. The humor is refreshing and light, making it a delightful watch.

Some fans even shared that it’s one of the best romantic comedies in recent years. As always, Ray Romano, Emily’s dad, did not disappoint. His subdued yet witty performance shone throughout the film.

5. Captive State (2019)

English 1h 49m IMDb
Captive State (2019) Best Chicago Movies to Add in Your Watchlist

Rupert Wyatt 

Stars: John Goodman, Ashton Sanders, Jonathan Majors

This movie is an exciting and unique take on alien invasion. A Chicago neighborhood witnesses the aftermath of the extraterrestrial force invasion. Two sides of the community, the dissidents and collaborators, fight for their beliefs.

Many viewers believe this film is very much underrated. The actors, even those with more minor roles, gave solid performances. Alien stories have been made many times, but this one takes a different perspective.

It veers away from the heavy special effects characteristic of many sci-fi movies. However, it did not take away its edge and suspense. The tight pacing and camera shots made it riveting.

6. While You Were Sleeping (1999)

English 1h 43m IMDb
While You Were Sleeping (1999) Best Chicago Movies to Add in Your Watchlist

Jon Turteltaub

Stars: Sandra Bullock, Bill Pullman, Peter Gallagher

This romantic -comedy is like an ode to Chicago’s famous landmarks. Santa Bullock plays Lucy, a Chicago Transit Authority ticket booth worker. An unfortunate event on the tracks led to a coma patient’s family believing she was his fiance.

It’s a light movie you wouldn’t mind watching many times. It also cemented Bullock’s career as a rom-com star and placed romantic comedies in everyone’s consciousness.

It showed Chicagos’ warmth and beauty, especially during cold winter nights. It will make you want to hop on the plane and spend the holidays there. The film celebrates family relationships, love, and everything in between.

7. Win It All (2017)

English 1h 28m IMDb
Win It All (2017) Best Chicago Movies to Add in Your Watchlist

Joe Swanberg

Stars: Jake Johnson, Rony Shemon, Morgan Ng

New Girl’s Jake Johnson plays Eddie Garrett; a man addicted to gambling. He is broke and almost homeless until a friend heading to prison for a while leaves him a duffel bag of money.

He spiraled down when he used up all the cash and got into debt. This movie showcases everyday Chicago suburb living. It’s so realistic and relatable that you’re watching a neighbor live his life.

When a movie gets you so invested in a character, it means it’s good. You’ll catch yourself holding your breath toward the end with its suspenseful conclusion.

8. Southside With You (2016)

English 1h 24m IMDb
Southside With You (2016) Best Chicago Movies to Add in Your Watchlist

Richard Tanne

Stars: Tika Sumpter, Parker Sawyers, Vanessa Bell Calloway

Barack and Michelle Obama are iconic figures in world history. However, they were ordinary people who went on dates once upon a time.

This movie narrates how they first met with Chicago as the background. You’ll glimpse the former president’s life as a Harvard Law student and how his relationship with Michelle blossomed into something beautiful.

It’s a charming, witty, and inspiring love story – a refreshing deviation from cheesy romantic comedies. Fans revealed that it gave them the confidence to disclose their political views and cultural beliefs on the first date. And with John Legend at the helm, expect some pretty good music, too.

9. High Fidelity ( 2000)

English, Danish 1h 53m IMDb
High Fidelity ( 2000) Best Chicago Movies to Add in Your Watchlist

Stephen Frears

Stars: John Cusack, Iben Hjejle, Todd Louiso

This film is based on a cult-classic novel of the same title. It’s relatable to people who have had their hearts broken and want to forget about it with some pop music. One of the most common observations about this movie is that John Cusack is not acting.

He is living and breathing his character. It is maybe because he collaborated on the screenplay and created the soundtrack list for the film. It’s a perfect mix of excellent music, enjoyable acting, and the incredible Chicago landscape. Everyone seemed to have fun shooting this film, and it shows.

10. My Best Friend’s Wedding ( 1997)

English, French, Italian 1h 45m IMDb
My Best Friend’s Wedding ( 1997) Best Chicago Movies to Add in Your Watchlist

P.J. Hogan

Stars: Julia Roberts, Dermot Mulroney, Cameron Diaz

One of the most iconic scenes in My Best Friend’s Wedding is the lead star’s cruise over the Chicago River. It was Julia Robert and Delmont Mulrooney’s last dance before he married someone else.

This romantic comedy is a classic favorite reminder of simpler times. Once again, Roberts never failed to charm the audience with his self-deprecating humor and All-American girl charm.

It’s the movie you may have watched as a teen but would love to watch again with your teenage kids. It’s proof that fun, romantic films never get old.

11. Widows (2018)

English, Spanish, Polish 2h 9m IMDb
Widows (2018) Best Chicago Movies to Add in Your Watchlist

Steve McQueen

Stars: Viola Davis, Michelle Rodriguez, Elizabeth Debicki

A film led by award-winning actors can result in very high expectations- and this one did not disappoint. Viola Davis, a widow herself, leads other women whose husbands died in a botched heist.

They are continuing their husband’s dirty work before their lives get in danger. It’s a more profound, more serious girl power movie that shows the strength and grit of a mother cornered by her enemies.

Davis gave an astounding performance that shone through the screen. Other cast members, such as Michelle Rodriguez, Colin Farell, and Liam Neeson, were also terrific.

12. The Untouchables (1987)

English 1h 59m IMDb
The Untouchables (1987) Best Chicago Movies to Add in Your Watchlist

Brian De Palma

Stars: Kevin Costner, Sean Connery, Robert De Niro

This classic masterpiece depicts the fierce and exciting life of mob warlord Al Capone. In true Brian de Palma style, it reveals the life of the infamous mafia and how it lorded over 1930s Chicago.

It was during Prohibition that his gang ruthlessly supplied liquor illegally. Fans and critics agree that this cinematic marvel is a must-see.

You will expect no less when Robert de Niro and Sean Connery team up for a movie- it’s always a feast for the senses. The excellent story, the right amount of action, and the script created a film that’s still relevant today.

13. Candyman (1992)

English 1h 39m IMDb
Candyman (1992) Best Chicago Movies to Add in Your Watchlist

Bernard Rose

Stars: Virginia Madsen, Xander Berkeley, Tony Todd

Completing this list is a horror movie that’s unmistakably shot in a Chicago neighborhood. Candyman is one of the best 90s scary films. It’s so good that it spurred a sequel many years after.

Many fans revealed that it still haunts them days after watching the movie. When that happens, it means that the direction, storyline, and suspense were all excellently made.

The ending is unpredictable and will leave you terrorized. The pacing was incredible, making you stay on the edge of your seats. Lastly, tension is an ingredient for nightmares.


A movie is a great way to showcase a city’s landmarks and best features. This article’s 13 Best Chicago movies celebrate the Windy City’s neighborhoods, attractions, and people. It’s like taking a trip without leaving the comforts of your home.

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