Ten Awesome Movies Straight Out of Chicago

Candyman

There are plenty of movies set in Chicago, from Backdraft, the Barbershop franchise, The Boss, The Break-Up, the Child’s Play series, Damien: Omen II, Divergent, The Divergent Series: Insurgent, Eagle Eye, and The Fugitive to Hardball, I, Robot, A League of Their Own, Little Fockers, Mean Girls, Meet the Parents, National Lampoon’s Christmas Vacation, The Relic, Road to Perdition, What Women Want, The Watcher, and The Whole Nine Yards, and more. Now, although we would have wanted to get all these movies in on this list of Ten Awesome Movies Straight Out of Chicago!, we cannot, which is why we thought the next best thing would be to get you a mix of movies that give you a fleeting glimpse of what the City of Chicago is all about and how it has been represented in several movies from different genres.

Candyman

If gruesome killings are something you can digest, Candyman is sure to keep you entertained, and yes, if you are from Chicago or love the city, the mention of the Cabrini-Green housing projects of Chicago, which mark the beginning of the story, should be enough to get you hooked from the word go! Of course, several scenes of the movie were shot in different areas of Chicago too, including the Museum of Contemporary Art — this was the first feature film that received permission to shoot here — the North Park neighborhood, the Near North Side’s Marina City apartment buildings and condos, and even the puppet sequences featured in the film had a Chicago connection. Although the film suffered a setback due to the pandemic — the release dates were postponed several times before it was finally released on-demand — it managed to do quite well in terms of collections, raking in 77.4 million against the production of $25 million. Oh, and whatever you do, don’t stand in front of a mirror and repeat the word “Candyman” five times, especially if you find yourself in the city of Chicago! And if you find this a rather gruesome start to this list, don’t worry, we’ve got some refreshing ones up ahead!

Home Alone

If you thought only a high-school kid can have loads of fun by painting the town red, as Ferris Bueller did in the movie above, all you have to do is take a look at Home Alone to see just how even a kid can do all that and more, within the confines of his home, and at the expense of a couple of amateur thieves who just don’t know what they’re in for! Set in a suburban home of Chicago, the movie has the ever-cute Kevin McCallister, played by Macaulay Culkin, left behind by his family when they leave town to spend Christmas in Paris. And while Kevin discovers that he has indeed been left behind, what actually sets the ball rolling on the storyline is two thieves deciding to make the most of an apparently empty house and rob it when nobody’s looking. There’s just one minor detail they learn about in pretty embarrassing and hurting ways later — that there’s a child in the house who will stop at nothing to defend it from these amateur invaders! One of the most popular kids’ movies of all time, and enjoyed by adults as much too, Home Alone still has a connection in Chicago that’s often frequented by fans of the franchise — the Winnetka home that was featured in the film.

My Best Friend’s Wedding

We told you we’d bring you a variety of movies on this list and here we are with a romantic comedy that you can sit and watch on a Sunday afternoon to make your day an even more beautiful one! And you’d agree with us when we say there’s hardly a Chicago movie out there that’s better than My Best Friend’s Wedding to spend some quality time with a loved one, friends, or even family! With the beautiful Julia Roberts and Cameron Diaz leading the way on the femme fatale front and Dermot Mulroney at the center of the triangle — that isn’t really one if you take into consideration that one side of it just doesn’t go both ways — the movie is all about trying to keep your best friend from getting married to someone else, but eventually making the right choice for everyone. With loads of Chicago landmarks featuring throughout the movie to give viewers an opportunity at some sightseeing too, My Best Friend’s Wedding is all about the sunny side of Chicago, and of course, love, friendship, and all things beautiful!

The Blues Brothers

With John Belushi taking on the role of “Joliet” Jake Blues and Dan Akroyd playing his brother Elwood Blues, The Blues Brothers has plenty of Chicago landmarks featured in it, making the movie an easy addition to this list. From the Chicago City Hall building that plays host to iconic scenes in the movie to the Palace Hotel Ballroom, several landmarks from the city are well-used to give the storyline the thrill only a city like Chicago can offer it! Bringing to the screen a perfect blend of music and comedy, a combination few other filmmakers would dare to explore, The Blues Brothers has loads of twists and turns and adventures galore, and of course, music! With names like James Brown, Ray Charles, Aretha Franklin, and Cab Calloway III adding to the lilting tunes that play out in the movie, The Blues Brothers, although in itself more than just a collection of great music, does have enough to lure in even standalone music lovers.

The Barbershop Franchise

The south side of Chicago comes alive in the Barbershop franchise, and throughout the three direct installments — Barbershop, Barbershop 2: Back in Business, and Barbershop: The Next Cut — the franchise stays true to the city of Chicago, and even commits to specific elements that bring alive the good and the not so good of it. The only departure is the  Queen Latifah spinoff, Beauty Shop, which shifts base to Atlanta. A comedy franchise that inculcates in its sequences subtle and sometimes, in-the-face problems related to the generations as well as the changing face of Chicago and especially the south side, the Barbershop series tackles a lot of direct issues from tackling loan sharks and not giving in to bigger brands to competition in the neighborhood and gang violence. And all the time, it uses the effective medium of smart comedy to leave an impact. With Ice Cube and Cedric the Entertainer among those who make repeated appearances in the franchise and form the core of the storyline, the Barbershop is a funny yet thoughtful peek at life on the south side of Chicago.

The Untouchables

A gangster movie that redefined how gangster movies should be made, and certainly a title that was shouldered by yet another powerful and towering performance from the extremely talented, and in this case menacing, Robert De Niro, The Untouchables is what you show those who wish to know what it is to feel fear and dread even when they aren’t watching a horror movie. The sheer willpower of Al Capone to wield absolute power and truly believe that he and everything he has built is indeed above the law is showcased so breathtakingly and convincingly by Robert De Niro that one wonders if there was any way any other actor could have even come close to the performance. Although overshadowed by a mile, the other actors, including Kevin Costner, Sean Connery, Andy Garcia, Charles Martin Smith, and Billy Drago, also manage to make just the right amount of impact to aid Robert’s extraordinary performance. And while it is indeed heartbreaking that Robert did not manage to win an Academy Award for this portrayal, the city of Chicago sure wins when it comes to the depiction of several landmarks from the city making their presence felt in the movie.

Widows

The women of Chicago are one strong lot and if you have your doubts, all you have to do is watch Widows to put every one of your doubts to rest. With a powerful cast led by Viola Davis, Michelle Rodriguez, Elizabeth Debicki, and Cynthia Erivo, the movie revolves around the decision of four recently widowed women to try and set right the mistakes their husbands made while attempting to rob a crime boss. While the wholehearted support of an ensemble cast results in an impactful movie that certainly does justice to its powerful storyline, what stands out for us is that the film was set and shot in the city of Chicago, bringing to life the city’s hues and people. And although the movie ranks high on the popcorn entertainment front, it also clocks high numbers as far as the social message quotient goes. not every movie gets this balance but Widows sure does it just right to make sure that the audiences are not just well-entertained but gain awareness too.

While You Were Sleeping

An endearing romantic comedy that leaves you smiling and happy for all that life offers even when it seems like its taking things away from you, While You Were Sleeping is all about love and care, compassion and understanding, and more! And that’s not the only thing that has helped this one onto this list! What makes this one an extra special addition to this list is its direct connection with the Chicago Transit Authority — after all, the role played by Sandra Bullock in the movie depicts a good-hearted yet lonely Chicago Transit Authority token collector saving a man’s life, and after he slips into a coma, falling in love with his brother and even establishing a fraudulent yet genuine relationship with his family. Well, the plot may sound a tad complicated but hey, love is indeed complicated at times! With charming Bill Pullman to keep her company, Sandra proves that even when someone is living a boring life as a Chicago Transit Authority token collector, life can just spring a surprise and take them on a whirlwind fun yet emotional ride. For us, the Chicago connection and a happy ending are all it took to add While You Were Sleeping to our list!

Ferris Bueller’s Day Off

Ferris Bueller’s Day Off is one of those movie experiences where nothing, not the teasers, not the trailers, not the raving reviews, and not even a scene-by-scene account from someone who has loved it, can do justice to all that energy and spunk that you witness in the movie. Oh, and when it’s a young Matthew Broderick leading the way, how can you even get all that cuteness and naughtiness into any other medium than the movie itself! Set in Chicago and showcasing just how much a young high school kid who’s only looking for a good time can accomplish in only a matter of a day, the movie’s storyline sure is as innovative as its sequences, and those are not even the only brilliant elements about Ferris Bueller’s Day Off. Whether it is the regular breaking of the fourth wall throughout the film, which helps the audience connect even more with the charming Ferris Bueller, or the fact that the movie was an all-out dedication to the city of Chicago, whatever worked for the film worked in the best ways possible. Oh, and why do we say this film was dedicated to Chicago? Well, the writer, director, and co-producer of the film John Hughes made that pretty clear when he openly said that through the film he wanted to capture as much of Chicago as he could, “not just in the architecture and landscape, but the spirit.”

Divergent and The Divergent Series: Insurgent

Although the third installment of The Divergent Series — The Divergent Series: Allegiant was shot in Atlanta, the first two installments of the franchise — Divergent and The Divergent Series: Insurgent — were very much a Chicago affair throughout. Revolving around the idea of a futuristic society where all residents are divided into distinct groups based on their virtues, and the lot that doesn’t really fit into any and are labeled Divergents, the movie creates an alternate social parallel that although a tad difficult to comprehend in the beginning, lures you in later. While the first of the series is all about discovering and gaining an understanding of what they are all about, the second part of the series deals with an uprising and associated consequences and challenges. While Shailene Woodley, Theo James, Zoe Kravitz, Miles Teller, Ansel Elgort, Ray Stevenson, Ashley Judd, Mekhi Phifer, and Maggie Q played their roles throughout the trilogy, other actors made their own share of appearance in either two parts of the trilogy or just one, including Kate Winslet, Jai Courtney, Ben Lloyd-Hughes, Tony Goldwyn, Justine Wachsberger, Naomi Watts, Octavia Spencer, Keiynan Lonsdale, Jonny Weston, Jeff Daniels, Bill Skarsgard, Christian Madsen, Any Newbold, Ben Lamb, Daniel Dae Kim, Suki Waterhouse, Rosa Salazar, Emjay Anthony, and Janet McTeer. And although the films in the series kept plummeting in terms of popularity, we are just glad to see the Chicago angle being explored to the hilt in the first two parts — Divergent and The Divergent Series: Insurgent. 

Let’s Wave Chicago Goodbye For Now!

From Robert De Niro wreaking havoc throughout the city with the help of the grip he has on the city to the Divergents protecting the only city they’ve called home, Chicago sure serves out backdrops that suit films from crime dramas and sci-fi thrillers to love stories and out and out comedies. And when a city is as versatile as this one, you know there’s a lot more to it than meets the eye or makes the screen. Here’s waving goodbye to a city that we hope to see more and more of in many more films to come! Goodbye, Chicago!

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