City of Big Shoulders and The Big Screen

Start your road trip with a guided tour through some of Chicago’s most iconic film locations by Chicago Film Tours. Notable stops include the Willis Tower, the tallest building in the Western Hemisphere, which has been featured in box-office hits like The Dark Knight, Divergent, Ferris Bueller’s Day Off and Rampage. While you’re at the Willis Tower, be sure to check out the 103rd floor where you can find Skydeck Chicago, the highest observation deck in the US. Make another stop at the Art Institute of Chicago. Here, you can marvel at impressive artwork by Chagall, Dalí, Matisse, Picasso, and Pollock—just like Ferris, Sloane and Cameron did in Ferris Bueller’s Day Off. Stroll downtown to the Richard J. Daley Center and Plaza which features the famous statue gifted to Chicago by Pablo Picasso. The statue is included in popular movies like The Fugitive, Stranger than Fiction, The Blues Brothers and the iconic parade scene of Ferris Bueller’s Day Off. 

More nearby movie and TV locations to discover include Chicago City Hall (featured in The Blues Brothers), Buckingham Fountain, a historic landmark featured in the TV show Married with Children and found in Grant Park. Grant Park is known as “Chicago’s Front Yard” and has its own claim to fame after being featured in films like About Last Night and -– you guessed it – Ferris Bueller’s Day Off! With so many noteworthy film and TV show locations in Chicago, it’s no wonder the city is home to several film festivals each year, including the Chicago International Film Festival and the Chicago Latino Film Festival. 

There are plenty of Chicago restaurants that have also been featured on screen as well. Just across from the Art Institute, you’ll find The Berghoff, a historic family-owned German restaurant that was featured in The Dark Knight. You’ll be able to discover even more Chicago Batman filming locations soon enough as the next film of the series is to be released in 2022.

Head to Navy Pier on Chicago’s lakefront to grab delicious deep dish pizza at Giordano’s or a  famous “Cheezborger” at the Billy Goat Tavern, the restaurant chain that inspired a Saturday Night Live sketch. Navy Pier itself has also been featured in movies like The Dark Knight, The Color of Money, and the thrilling “Capture the Flag” scene of Divergent that takes place on the Pier’s famous Centennial Wheel. 

Back downtown, you can hop aboard an architectural boat cruise along the Chicago River, just like the one Julia Roberts takes in MyBest Friend’s Wedding, to spot even more movie and TV gems around Chicago. Locations include the DuSable Bridge, featured in The Untouchables, the Clark Street Bridge, featured in Office Christmas Party and Chicago Union Station, featured in films like The Sting, My Best Friend’s Wedding, Public Enemies and Derailed. Not far from Union Station is the Chicago Board of Trade which has been featured in several films like, Batman Begins, Transformers: Dark of the Moon and more. 

Have dinner at Smith & Wollensky – located along the Chicago River and known for their mouthwatering steaks, this restaurant was featured in the romantic comedy The Break-Up. Get some rest after a long day of sightseeing. The Blackstone Hotel, located along Michigan Avenue was included in the movies The Untouchables and The Color of Money; the Hilton Chicago can be spotted in movies like The Road to Perdition, The Fugitive and Little Fockers. The posh Drake Hotel, known for its sweeping views of Lake Shore Drive and Lake Michigan, was famously featured in My Best Friend’s Wedding as well. If you’d like to get a head start on day two’s festivities, head north to the Wrigleyville neighborhood to stay at Hotel Zachary, located just across from Wrigley Field, home of the Chicago Cubs.

On day two, venture further north into some of Chicago’s most charming neighborhoods that have set the scene for even more beloved Illinois films and TV shows. Lincoln Park is home to one-of-a-kind attractions like the free Lincoln Park Zoo where you can spot nearly 200 unique animal species. There’s also the Chicago History Museum, where you can learn about the city’s storied past. Both are featured in the romantic comedy, Return to Me. Inside the Chicago History Museum, stop at North & Clark Cafe to enjoy a quick and delicious breakfast. 

Along Armitage Avenue, featured in The Break-Up, you can browse quaint boutiques and perhaps pick up something to remember your trip by. Lincoln Park’s not just featured in rom-coms, though! Not far from Lincoln Park Zoo, you can stroll past the house used in The Fugitive as the home of Dr. Richard Kimble (336 W. Wisconsin St.) as well as the Biograph Theater. It was here that notorious Chicago gangster John Dillinger was killed, with the location being used as one of the sets in the film Public Enemies, detailing Dillinger’s life. Also in Lincoln Park is the Steppenwolf Theatre, which was founded in 1976 by actors Gary Sinise, Terry Kinney and Jeff Perry and boasts plenty of notable past ensemble members like John Malkovich, Laurie Metcalf, John Mahoney and Joan Allen.

Next, head to The Second City where so many legendary comedians got their start and eventually made their way to Saturday Night Live including Mike Meyers (Wayne’s World and Austin Powers), John Belushi (The Blues Brothers and Animal House), Tina Fey (30 Rock and Mean Girls), Bill Murray (Groundhogs Day and Ghostbusters) and Jane Lynch (Glee, The Marvelous Mrs. Maisel and A Mighty Wind.) You can also spend a day at the ball game at perhaps one of Chicago’s most-used film locations, Wrigley Field. It’s been featured in iconic movies including Ferris Bueller’s Day Off, The Break-Up, A League of Their Own, Rookie of the Year, The Blues Brothers, Sleepless in Seattle and more. And with so many stars wanting to pay a visit to the “Friendly Confines” to sing during the seventh inning stretch, Wrigley Field is also one of the best locations in Chicago to spot film and television stars in the flesh!

For dinner, head to Twin Anchors in Old Town, featured in films like The Dark Knight and Return to Me. It’s an old-school barbecue joint (with seriously good ribs) that was founded in 1932 and once frequented by Frank Sinatra. Head north to catch a show at one of the city’s most iconic theaters/music clubs like Music Box Theater in Lakeview (High Fidelity), Riviera Theatre (The Break-Up) or Green Mill Tavern in Uptown - an Art-Deco jazz club with a storied speakeasy past, dating back to the days of prohibition (The Dilemma and High Fidelity).

End the day with a nightcap at Lottie’s Pub, featured on TV regularly as “Molly’s Bar” on Chicago PD, Chicago Med and Chicago Fire - or Skylark, used in the movie The Break Up.

For the last day of your road trip, choose your own adventure out to the suburbs surrounding Chicago, depending on which direction you’re heading to next. 

If you’re heading south, take a drive down the iconic Route 66, that starts right in downtown Chicago (at the corner of Adams Street and Michigan Avenue), to Joliet. Before you head out of the city, stop by Lou Mitchell’s, a Chicago institution that has been featured on Chicago PD and is known for delicious diner-style breakfast and their signature mouthwatering donut holes. Plan a visit to Old Joliet Prison that once housed infamous criminals like Leopold, Loeb and Gacy. The prison has also been a filming location for movies and TV shows like The Blues Brothers and Prison Break. Old Joliet Prison is now reborn as a tourist destination offering guided history tours for visitors, some led by former prison guards! Stop for lunch at Thayer Brothers Deli & Grille in Joliet, owned and operated by 1985 Chicago Bears Super Bowl champ Tom Thayer and his family, known for their mouthwatering chicken noodle soup. Don’t forget to snap a pic at the Blues Brothers bench at the Joliet Area Historical Museum, an Illinois road trip must! 

You can also head north from Chicago to enter into John Hughes’ movie territory, an iconic 80’s film writer and director who was known for filming his movies on site around the Chicagoland northern suburbs. Make sure to stop for lunch or dinner at Hackney’s on Lake in Glenview, home to the “Original French Fried Onions” and signature reuben sandwich. 

In Winnetka, drive past the picturesque home featured in the beloved holiday comedy classic, Home Alone (671 Lincoln Ave, Winnetka). Not far from there in Wilmette, you can drive past Trinity United Methodist Church which was also used in the movie. While both of those locations were used for exterior shots of Home Alone, not many people realize that the entire interior of the film was shot on a set built inside the New Trier High School gymnasium in Northfield! Rumor has it the Home Alone crew had the idea to film there after shooting another one of John Hughes’ famous movies there, Uncle Buck, featuring the cherished late comedian John Candy.

More northside areas to add to your tour includes spotting Glencoe Union Church (Sixteen Candles), shopping at Northbrook Court (Weird Science) and marveling at the mid-century modern style-home in Highland Park that was the setting for Cameron Frye’s house in Ferris Bueller’s Day Off (370 Beach St., Highland Park). While your Illinois movie and TV road trip won’t end in a freeze-frame like most John Hughes’ films, we hope you're able to freeze your favorite stops with tons of pics to enjoy for years to come!