The Sting

Paul Newman and Robert Redford. Need I say more?
The Sting is one of their best. The film is one of everybody’s favorites.

Set in 1936 Chicago, The Sting portrays two grifters, Henry and Johnny. They not only con the villain—Doyle—but also in scene after scene, they trick the viewers as well.

You’re an idiot if you haven’t seen this movie.

Some Like It Hot

This movie is still hilarious in 2020. Marilyn Monroe can act!
In the prohibition-era Illinois and in winter, two starving musicians by chance witness the Valentine’s Day Massacre.
Escaping with only their lives but losing their musical instruments, our feverish duo is compelled to take it on the chin.
The two dress up as women to hitch a ride with an all-woman orchestra and head to the Sunshine State.

Then enters Sugar Kane (played by Marilyn Monroe), an enchanting combination of sexy and innocent.
When the two boys (dressed as girls) cover for Sugar when she got caught with booze, Sugar feels an instant bond with the two boys (posing as girls).

Above The Law

In the film Above The Law, shot in Illinois, the action is great and the martial arts are ahead of its time; not to mention this film straddles many levels of meaning. Steven Seagal has a great face for an action hero actor, but his voice sounds brittle and he runs like a girl.

Toscani, played by Seagal, must rise above the law (like in all his movies) to stop the corrupt police force and CIA who are above the law. When the law behaves unlawfully, then it’s up to Toscani to take matters into his own hands.

I found that, during wartime, Toscani’s concern when witnessing torture of prisoners was overdone and mismatched with his brutal treatment of a teenage boy who gave drugs to his (Toscani’s) niece. Maybe Toscani was a softy wussbag back in his war days and later got more ruthless.

Airplane!

Leslie Nielson started as a serious actor, but he’s now best known for silly—but hilarious—movies like Airplane. In Airplane!, the one man with a fear of flying is forced to save a plane and land it in Illinois safely when both the pilots get food sick.

If you’re a little wary about films that have an exclamation point in the title, fear not. Without doubt, Airplane! is one of the most hilarious films ever put to print. The picture comprises a string of funny scenes that thread together a gossamer plot. However, in Airplane!, the comedy is so superb that it conceals the paper-thin plot.

This movie is filled to the brim with zingers: zingers which you can and will use, if you want to be funny.

Backdraft

One of the best movies set in Chicago Illinois about firefighters, Backdraft confirms that Ron Howard is a heavy hitter in Hollywood. Starring Kurt Russell and Alec Baldwin’s brother, the acting is top notch, the tone is sentimental, and the special effects were the best of 1991.

Bad Teacher

Cameron Diaz portrays a typical teacher in Chicago IL. From what I’ve heard, the film is not funny and not worth viewing.
Normally I personally don’t care whether a picture is predictable, but in Bad Teacher there is no laughter to make up for it, and the dialogue is uninspired.

The Bourne Legacy

The culmination of the Bourne saga ends in the Windy City—i.e., Chicago .
Though this picture is not quite as good as the masterpiece that is the Bourne trilogy (that would be near impossible), this film bobs up and down on the resulting ripples that happened because of The Bourne Ultimatum.

Ferris Bueller’s Day Off

A classic, one-of-a-kind movie that will still make you laugh even after watching it a dozen times.
Aspiring high school drop-out Ferris hates school, so he skips class and takes his girlfriend Sloane and his friend Cameron to downtown Chi-Town.

The ways he skips school and gets his friends in trouble is always devious and clever.
The redhead principal soon catches on to Ferris’ skipping and playing hooky, and tries hard (and consistently fails) to catch Ferris.

Throughout the comedy, Ferris Bueller’s character develops, discovering parts of himself he hadn’t noticed before.
His bitter, vengeful sister cannot comprehend how Ferris gets away with his antics. Ferris Bueller was taped in Chicago Illinois.

The Fugitive

In the classic The Fugitive—shot in Chicago Illinois—Harrison Ford plays Richard—a man falsely accused of murdering his wife.
His goal is to find the man who killed his wife, and in the process vindicate himself.

Even if you’ve seen this film 10 times, it will still surprise you when you watch it again.
The acting, the dialogue, and the action are all superb.

The Lake House

A beautiful film with a moving sci fi element. I’m not ashamed to say I love this picture.

I love motion pictures with time travel in them (another on this list, The Time Traveler’s Wife).
A good sci fi movie makes you care about the characters in the movie more than the sci fi element, and The Lake House—set in a suburb of Chicago—does this masterfully.

I, Robot

Loosely based on the Isaac Asimov novel, I, Robot stars Will Smith in this sci fi drama as he battles robots in 2035 era Chicago Illinois. It’s an excellent movie, and gets better with age (in 2023 it’s especially good).

Chicago

No list of Chicago IL movies would be complete without the obvious movie titled Chicago.
Richard Gere and John C. Reilly star in this outstanding remake of a classic musical.

Watching this picture is like sitting in the audience of a broadway play (though I’ve never done either).

Meet The Fockers

Filmed in Chicago IL, this is a funny sequel to Meet The Parents.
This motion picture stars Owen Wilson, so it will make you laugh a lot. Odds are it has more chuckles than Meet The Parents, though the chuckles aren’t as hearty or subtle or fresh. Like many sequels, it has several scenes that are simply different versions of the original film, including the puns on “focker,” the cameo from Owen Wilson, the pet incident, the sports competition incident, and the dinner incident.

My Best Friend’s Wedding

Many girls cite this as their favorite movie, but it’s enjoyable for guys to watch it as well; especially if you live in Illinois because (wait for it…you don’t know what I’m gonna say) this was shot in Illinois.

Rupert Everett walks like a panther. Throughout the picture he offers his friend sensible advice and sticks by his friend. You’ll enjoy this movie each time you watch it. In the end, the ending wasn’t really sad. Julia wouldn’t have been happy with Dermot’s rigid schedule anyway. When she walks free in the end, though she didn’t achieve her goal, she realizes it’s not what would really make her happy. In the end she remains single, which is life. Sometimes you have to let go of someone you love and face life on your own.

There’s no prince appearing on a magic carpet the day you become single,
but maybe a prince on a magic carpet wouldn’t really make you happy like you expect.

National Lampoon's Christmas Vacation

One of the funniest movies ever, and almost certainly the funniest Christmas movie ever made.
In cinema history, the screenplay is among the most intelligent, sharp, and hilarious. Without a doubt the direction and pacing is inspired. It captures the essence and ambiance of a family gathering and the spirit of Christmas. Everyone in the dream cast has superb comic timing and exhibits great talent. This motion picture was set in Chicago Illinois of all places.

Parker

This 2013 remake of the best movie of all time Payback (1999), though not quite as good as Payback, is still great in its own right. Moreover, Parker takes place in Chicago IL.

Many people criticize Jason Statham for always doing the same role, but personally I couldn’t care less how versatile an actor is.
I don’t watch a movie to see how talented or versatile an actor is. I watch a movie to enjoy the movie. If the acting is good, I’m happy.

In Parker, Statham plays Parker, a thief.
But a thief who doesn’t steal from those who can’t afford to lose what’s stolen, and a thief who doesn’t hurt people if they weren’t asking for it.

As in the original Payback movie, Parker is doublecrossed by his partners and left for dead.
The bulk of the picture is his revenge.

Planes, Trains and Automobiles

This is both a comedy and a drama, and will move you to tears. One of my favorite movies.

Chicago businessman Neil Page (played by Steve Martin) tries to get home for the holiday of Thanksgiving, but throughout this movie he has the worst luck.

Even worse, he can’t get rid of shower-curtain-ring-salesman Del Griffith.
The film is one of those where two opposite people are forced to be confined together (forget what that’s called), which is funny.
But in the end we learn that Del has a secret.

Primal Fear

Ed Norton and Richard Gere have great chemistry in Illinois throughout this well-crafted film.
The acting is top shelf throughout. Richard Gere achieves the goal of any actor—making the viewer care about the sort of person we generally dislike.
For a 2 hour movie, the plot is intricate and tight, with perfect pacing, never too fast or too slow.

Public Enemies

This is one of those movies I wish everyone watched, whether in or out of Illinois. It’s beautiful.
Johnny Depp plays John Dillinger.

During the Great Depression, people were suffering and crime was on the rise.
For most, it was a time of despair and desperation. For John Dillinger, it was a time of opportunity.

Depp portays Dillinger flawlessly—a man that adapted well to the era as only a Chicagoan in 1933 could.
The story is fascinating and the action is fun.

Raw Deal

At his peak, Schwarzenegger is a juggernaut one-man army as he collapses a Chicago crime family with one hand tied behind his back.
For what it strives to be, this is a great picture.
Not only is it an action film, but also the action is propelled by a captivating storyline that keeps the viewer hooked.

Road to Perdition

This film is beautiful and haunting, and the setting is Chicago Illinois.
Though the first 15 minutes are slow-going, the whole cast gives faultless performances.
This may be Tom Hanks best work.

Paul Newman gives the best performance in the film, though his character has an Irish accent, Newman, as always, played the role perfectly, never overdoing it or underdoing it.

Sleepless in Seattle

When you think romantic comedy, this is the movie that comes to mind.
The film is starts in Illinois where Sam (played by Tom Hanks) lives with his son Jonah.
To escape the memories linked with his wife’s death, Sam decides to move away from Chicago and settle in Seattle.
The son Jonah wants his father to find a new wife, but Sam hasn’t even begun to think about dating again.

Stranger than Fiction

An odd film about a man whose life is narrated—literally. He can hear the narration.
Harold (played by Will Ferrell) had been a boring IRS auditor based out of Illinois, when one day he wakes to discover his life is audibly narrated.
Then he meets the author who is writing his life.

Stranger than Fiction was Will Ferrell’s first foray into a dark comedy—away from the bang-you-over-the-head comedies.
The film combines existential philosophy with cookie-cutter comedy.

This Is Spinal Tap

Maybe the first mockumentary, This Is Spinal Tap is legend and still one of the best mockumentaries set within Chicago IL.
While still respecting the music of the rock and roll universe, the film presents the absurdity of it all.
All aspects of the music scene is ridiculed: the volume, the Beatles, the has-beens, the crybabies backstage, the arrogance. It’s as quotable as Airplane!.

If you hate music as much as I do, you need to see This Is Spinal Tap.

The Time Traveler's Wife

This is another of my favorite films.
It’s a sci fi film, and like all good sci fi films, it will make you cry.

A Chicago librarian, Henry (played by Eric Bana), was born with a gene that makes him time travel involuntarily, which results in marital complications. The way I just summed up it, it sounds like a comedy, but just watch it. It’s more of a tragedy.

Tommy Boy

So idiotic that it can only be hilarious, this movie is a comedy classic.
The bumbling imbecile Tommy, played brilliantly by Chris Farley, heads out on the streets with his father’s protege to raise funds so that they can salvage the family business from Chicago Illinois misfortunes.

Uncle Buck

John Candy aced every movie he acted in, but this heartwarming comedy tops the lot.
It’s safe to say this movie is a triumph not because it takes place at Chicago IL, but mainly because John Candy was Uncle Buck.

Wayne’s World

Party on! Insanely popular when it first came out, Wayne’s World is a great comedy.
Wayne and Garth (played by Mike Myers and Dana Carvey) host a cable TV show out of their basement.
Their ship finally comes in big time when their show catches a big break and goes commercial, but executive in charge Kane may have something sinister in mind. Though you’ll no doubt remember Aurora Illinois, Chicago IL is where this motion picture was taped.

What Women Want

This Illinois rom com proves once and for all that, given most women’s general inability or refusal to communicate, the only way for men to understand what women want is to become mind readers.

Nick (played by the greatest actor of our time, Mel Gibson), is the sort of man that women want and other men admire.
Now one day, Nick got himself electrocuted in his bathtub.

Sometimes when that happens, instead of dying, you develop telepathic abilities—you can now become a mentalist.

When he goes to work the next day, he discovers that women don’t care for him as he’d thought.

This rom com was done in Illinois.

When Harry Met Sally

This romantic comedy—shot in Chicago Illinois—will keep you hooked on the characters from beginning to end.
If this were a book, it would be a page-turner.

While You Were Sleeping

A nobody working for Chicago Transit Authority as a token collector in Illinois (played by Sandra Bullock) is mistaken for the fiancee of an important hospital patient in a coma (played by Bill Pullman).

This motion picture set in—Chicago Illinois—makes you believe in following your dreams and makes you believe in fate, so be careful.
The picture is sentimental and romantic, and Bill Pullman and Sandra Bullock have chemistry. Best time to watch it is when it’s cold outside.