Chicago in the Movies: See Where John Cusack, Julia Roberts and Sandra Bullock Filmed in the City of Big Shoulders

Casey Barber, Good Food Stories
Casey Barber, food writer/recipe developer and editor of Good. Food. Stories

Editor’s Note: Today’s guest post is written by Casey Barber, a freelance food writer/recipe developer and the editor of the online magazine Good. Food. Stories. Read on for some of her favorite Chicago film locations…

Doesn’t it always seem like New York City always gets the starring role in the movies? From ‘Ghostbusters’ to ‘Breakfast at Tiffany’s to, um, ‘Manhattan,’ the city has become an almost clichéd stand-in for the hopes, dreams, fears, and realizations of so many classic characters.

This incredible New York Movie Map from the site Alien Loves Predator gives you a sense of how many films have used the island as a supporting player. There are 91 movies on the map, and that’s just scratching the surface of what’s been filmed or set in NYC!

And then there’s Chicago, the perennial Second City. Though its celluloid star shines a little less ostentatiously than that of the Big Apple, it’s been the backdrop for a perfect cinematic moment or two over the past few decades.

I moved to Chicago from the rolling fields of western PA (cue Slap Shot) at the dawn of the 21st century to attend journalism school at Northwestern University. During my El-propelled travels throughout the city’s neighborhoods, I didn’t find any mobsters, showgirls, or Blues Brothers, but I did find an unshowy but striking vitality unlike the bombast that seems to overtake Manhattan on a regular basis.

Herewith are my favorite movies that capture the everyday grandeur I felt as a temporary citizen of the city of big shoulders.

High Fidelity

Though Nick Hornby’s book was set in London, John Cusack smartly changed the venue to his hometown of Chicago when he secured the movie adaptation rights, and thus made it one of the very few book-to-film transitions that actually improved on the original.

Championship Vinyl from 'High Fidelity'
John Cusack owned Championship Vinyl in ‘High Fidelity’

Championship Vinyl, the record store owned by Cusack’s character Rob Gordon, is unbelievably still a vacant building at the corner of N. Milwaukee and Honore in Wicker Park. The neighborhood was just gentrifying when the movie was filmed almost 15 years ago, and now it’s hipster city. Rob and his cronies would have done much better business these days.

Championship Vinyl Today from 'High Fidelity'
Championship Vinyl today – looks kind of lonely, doesn’t it?

The movie really is a subtle love letter to the city’s robust music scene, with references to classic clubs Schuba’s, The Double Door and Lounge Ax, and stickers from Chicago bands like Veruca Salt, the Falling Wallendas and Apocalypse Hoboken plastered all over the interior of Championship Vinyl.

Best of all, a few prominent scenes are set in The Green Mill, one of the greatest jazz clubs/bars in the city. You can’t miss the blinking neon sign on upper Broadway; step inside for the rococo decor and elaborately framed murals above the booths. It’s a trip. [Buy [amazon_link id=”B00003CXGA” target=”_blank” container=”” container_class=”” ]’High Fidelity’ on Amazon[/amazon_link]]

Green Mill from High Fidelity
The Green Mill from ‘High Fidelity’

While You Were Sleeping

Sandra Bullock’s cute little movie about a lonely El attendant gets major points for its opening credits chockablock with beauty shots of the city: from the Hancock Building and the Sears Tower (I will never call it anything else) to the clock on the old Marshall Field’s building (now a Macy’s, booo!) to the Picasso sculpture in front of Daley Plaza and a nod to His Airness, Michael Jordan.

The Randolph and Wabash stop in the Loop, where Sandra’s character Lucy works the tollbooth, is another authentic location that remains comfortingly shabby. Though renovations and improvements pop up here and there, most of the elevated platforms are still wooden, even those in the main Loop, and the tollbooths are still sort of there, even though we all use swipey cards now.

While You Were Sleeping, Randolph Wabash, Sandra Bullock
Sandra Bullock in ‘While You Were Sleeping,’ waiting for that one special token at the Randolph and Wabash stop in the Loop

Bonus points for knowing that the doctor who attends to Peter Gallagher in the hospital was played by John Cusack’s dad! (Yeah, he’s got a bit part in ‘High Fidelity,’ too.) [Buy [amazon_link id=”6304765266″ target=”_blank” container=”” container_class=”” ]’While You Were Sleeping’ on Amazon[/amazon_link]]

Ferris Bueller’s Day Off

OK, so maybe most Chicago residents don’t get to sing in a parade float on State Street, but then again, most Chicagoans probably can’t motivate an instantaneous grassroots movement to save their not-so-ailing selves. Out of all the John Hughes movies set in and around the Chicago suburbs, ‘Ferris Bueller’ is the one that takes best advantage of the city scenery, with scenes at Wrigley Field, the Art Institute, and of course, a sweet Ferrari ride down Lakeshore Drive.

There is no real-life Abe Froman, the Sausage King of Chicago, I’m sad to say. [Buy [amazon_link id=”B000BNX4MC” target=”_blank” container=”” container_class=”” ]’Ferris Bueller’s Day Off’ on Amazon[/amazon_link]]

My Best Friend's Wedding, Chef Charlie Trotter
Chef Charlie Trotter cooks it up in ‘My Best Friend’s Wedding’

My Best Friend’s Wedding

This one’s for the foodies: back in the day, before Grant Achatz changed the world through molecular gastronomy at Alinea, before pork bellies and pig’s ears gave an upscale connotation to Chicago’s former stockyard output at The Purple Pig, there was a guy named Charlie Trotter, who had — still does, in fact — a lushly elegant eponymous restaurant on Armitage Avenue.

Chef Trotter, by all accounts, is an understated perfectionist, so what’s he doing making a cameo in the opening moments of a slightly ridiculous rom-com that imagines Julia Roberts to be a 28-year-old food critic? God knows, but I almost choked on my homemade truffle-salted popcorn when I realized what I was seeing.

Untouchables, Julia Roberts' butt
Julia Roberts’ butt takes center stage on the Union Station stairs in ‘My Best Friend’s Wedding’

And for another edition of Chicago films overlapping, Julia Roberts gets to chase her would-be beloved, Dermot Mulroney, down the very same Union Station stairs that earned a place in movie history for the suspense-building baby carriage sequence in ‘The Untouchables’ (the scene below gets really good around the 5:15 mark):

Of course, Julia’s butt — not the beautiful stairs — gets most of the focus in ‘My Best Friend’s Wedding.’ [Buy [amazon_link id=”B00005JG6N” target=”_blank” container=”” container_class=”” ]’My Best Friend’s Wedding’ on Amazon[/amazon_link]]

Never Been Kissed

This one’s for the architectural nostalgists: in yet another slightly ridiculous offering starring Drew Barrymore as a socially inept Chicago Sun-Times copy editor who went to Northwestern (and gets her own office – what??), I strongly suspect most of the movie was not filmed on location in the Windy City.

But my post-grad journalism pride gets the best of me, and I’ve got to include the film’s loving exterior shots of the old Chicago Sun-Times building, which was sold in 2001 to a certain New York real estate magnate who goes by the name of Donald Trump. He tore the squat little mid-century building down, as you’d expect, and replaced it with a gleamingly bland tower. Sigh.

Never Been Kissed, Chicago Sun-Times
Drew Barrymore scored her own office at the Chicago Sun-Times in ‘Never Been Kissed’

The Chicago Tribune’s crazy ornate Gothic tower across the river always got most of the architecture gawkers, but I’ll always have a soft spot in my heart for the old Sun-Times building, and for all the cinematic moments that remind me of my brief but indelible time in Chicago. [Buy [amazon_link id=”B00006ZXSL” target=”_blank” container=”” container_class=”” ]’Never Been Kissed’ on Amazon[/amazon_link]]

Screenshots: Casey Barber


15 responses to “Chicago in the Movies: See Where John Cusack, Julia Roberts and Sandra Bullock Filmed in the City of Big Shoulders”

  1. Good. Food. Stories. ( Avatar

    Did you know Charlie Trotter once made a cameo in a Julia Roberts flick? It’s true! But which #movie was it? #chicago

  2. Laura Martone Avatar

    Hey, Casey! I attended Northwestern University, too, and I actually watched John Cusack film a scene from HIGH FIDELITY while living in the Windy City – one of my favorite towns in America. Thanks for the stroll down memory lane!

    1. Jane Boursaw Avatar

      Oh very cool that you got to watch Cusack film! That doesn’t happen much here in Traverse City, although we’re starting to get more recognition from filmmakers because of the Traverse City Film Festival. Then again, I heard that the new governor is taking away Michigan’s film incentives – bad move!

  3. Living Large Avatar

    Love John Cusack. Love High Fidelity. Love Chicago. 🙂

  4. Jane Boursaw ( Avatar

    #Chicago #Movies: See Where John Cusack, Julia Roberts & Sandra Bullock Filmed #wsbr @GoodFoodStories

  5. Good. Food. Stories. ( Avatar

    Hey, I wrote that piece! 🙂 RT @reellifejane: #Chicago #Movies: Where John Cusack, Julia Roberts, Sandra Bullock Filmed

  6. Vera Marie Badertscher Avatar

    I love, love, love Chicago, and thank you so much Casey Barber for this list of movies. I’ve seen most of them, but missed a couple. I’ll remedy that soon.

  7. Kerry Dexter Avatar

    always appreciated the way While You Were Sleeping realy got the touch of Chicago ambiance. and now you have me thinking about movies filmed in places where I’ve lived and how the places have changed — or not. thanks, Casey and Jane.

  8. Sheryl Avatar

    Chicago is a terrific city and I’m excited to be going back there in November for a wedding. It’s been years. And I’m also excited to see that I’ve actually seen all these movies – minus one or two. Great flicks indeed.

  9. Alexandra Avatar

    I did not realize there were so many films featuring Chicago!

  10. ruth pennebaker Avatar

    Don’t know how many times I’ve seen Ferris Buehler — but clearly, it’s time for another viewing. Did you know Ferris Buehler is one of Dan Quayle’s favorite movies? Made me respect DQ just a little bit.

  11. Jennifer Margulis Avatar

    I’m a total movie buff but I don’t think I’ve seen any of these movies! I also love Chicago and am going there in August. Glad I have live streaming now. Off to watch some of these!!

  12. sarah henry Avatar

    Love this and not sure how I missed it. The movies, the architecture, the food facts. Will have to share with my Chicago friends. Love the pic of Casey too.

  13. Jimbo Avatar

    That scene from the Untouchables is just fantastic. It was great to go to Union station and see the actual stairway. Beauitiful building.

  14. […] Abe Froman, the Sausage King of Chicago, and marvel at Charlie Trotter’s movie debut with my cinematic tour of Chicago at Reel Life With Jane. Bonus points to anyone who can remember how Lucy likes her hot dogs in […]

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