Ferris Bueller’s Chicago: Reliving the ’80s in a city that never stands still

Why is it that the ’80s just keep on rolling?

Most retro flashbacks happen in 20-year cycles, but the ’80s — that bold, bright decade of synths, shoulder pads, Pac-Man and really odd music videos (think: “The Safety Dance,” among others) — keeps resurfacing in waves through TV shows, music, movies and pop culture.

It’s been a tough couple of years, so it’s really no surprise that people of all generations are feeling nostalgic for a more optimistic era with an easy-to-define aesthetic.

At TPG, we’ve always found packing a bag and embarking on a globe-trotting adventure is a fine antidote to troubling times. But for many people, it’s returning to simpler times, when the Commodore computer and the Sony Walkman were state-of-the-art and you could wear leg warmers in summer while singing along to power ballads, that helps distract from life’s daily stresses.

If you sift through the canon of 1980s cinema, there’s one film that captures the teen spirit as much (if not more) today as when it was released in 1987. Ferris Bueller’s adolescent dream of thwarting authority figures is played out in, arguably, the one and only American city that could match the “righteous dude’s” swagger, brio and can-do spirit.

Scan the internet and you’ll find tour companies that have crafted ’80s-movie-themed itineraries paying homage to the city’s famed landmarks and magical moments of movie lore: the demolition derby of “The Blues Brothers,” the underbelly of Gotham City and, of course, the cultural touchstones and museums of “Ferris Bueller’s Day Off.”

But what happens when you try to recreate the 1980s in a city that never stands still? How has the city changed, and is it for the better? And, how can you make the moments (and those sick days) count?

On a beautiful summer day in downtown Chicago, my teen son recruited a couple of buddies to play hooky and find out. We followed the now well-worn “Ferris Bueller’s Day Off” trail to relive a few of Chicago’s classic 1980s movie moments and discover the sights and the stories that make Chicago the best city in the U.S. — right here, right now.

A red convertible ‘so choice,’ you really have to pick 1 up

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For teens steeped in 1980s Ferris nostalgia, getting to downtown Chicago means just one thing: driving along Lake Shore Drive in a shiny, red convertible, lip-syncing to Yello’s “Oh Yeah” — one of John Hughes’ brilliant soundtrack needle drops.

A gorgeous 1961 Ferrari 250 GT California Spyder was the movie’s most memorable prop, summing up the cooler excess of the ’80s. Valued at around $11 million, only 56 were ever made and it cameoed in just a handful of close-up scenes. Since director John Hughes’ budget didn’t stretch to thrashing a collector’s piece Ferrari, three replica Modena GT Spyder Californias were used (and one destroyed) instead. One of the replicas sold at auction for $409,000 in 2020, according to car auction company Barrett-Jackson.

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Renting even a faux Ferrari for the day was not going to make it through an expense report, but a cherry red convertible Ford Mustang was sick enough to satisfy the teen dream — until we found ourselves stuck in 8 a.m. gridlock on Lake Shore Drive and never hit speeds above 30 mph.

After a fun (albeit very brief) cameo, the Mustang sat for the day in a very expensive parking lot.

Nowadays, you wouldn’t dream of renting a car to explore downtown Chicago. Strolling the downtown Loop on foot, riding a bike or scooter along the lakefront, or taking the L train to explore Chicago’s neighborhoods is the best way to experience the city’s diversity, energy and vision.

Related: A classic getaway: Revisiting Chicago childhood favorites with my parents

Willis Tower: ‘Anything is peaceful from 1,353 feet’

Visit a metropolis with any teen and they will always gravitate toward superlatives. During the age of Ferris, the black-sheathed Sears Tower, built in 1973, was the world’s tallest building, a distinction it would hold for nearly a quarter-century. Today, it ranks 23rd, with Dubai‘s Burj Kahlifa (2,717 feet) holding the top spot since 2010.

Rising above what was, and still is, unquestionably one of the world’s finest collections of modern architecture, the trailblazing skyscraper has become shorthand for Chicago’s grit. All the big-name architects are here — the skyscraper prototypes of Louis Sullivan, the modernist minimalism of Ludwig Mies van der Rohe, the Prairie Style of Frank Lloyd Wright and, since 2004, the billowing steel of Frank Gehry’s show-stopping Jay Pritzker Pavilion.

The sweeping views from the 103rd-floor Skydeck expand across four states (on a clear day), and Ferris’ musing that “anything is peaceful from 1,353 feet” still holds true.

But Bueller, Cameron Frye and Sloane Peterson didn’t have the thrills and Instagram-induced theatrics of the Ledge, a collection of three glass-bottomed boxes that jut out from the Skydeck and inspire the obligatory selfies and unfiltered BeReal moments. There’s also a new interactive experience that opened last year. It traces the history of the city and the far-reaching impact of the Great Chicago Fire of 1871.

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A timed-entry system is now in place so, unlike Bueller, you can’t just wing it and show up at Willis Tower. If you want to experience the views without the crowds, reserve your tickets for 9 a.m. and be the first group to take the elevator.

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Related: Book this, not that: Get the most value from your hotel points in Chicago

The Art Institute of Chicago: ‘A person should not believe in an -ism’

Built for the World’s Columbian Exposition in 1893, the Art Institute is one of the finest museums in the country, famous for its world-renowned impressionist and post-impressionist collection filled with masterworks by Claude Monet, Édouard Manet, Pierre-Auguste Renoir, James Abbott McNeill Whistler and Edgar Degas.

In “Ferris Bueller’s Day Off,” John Hughes provides a flash tour of the museum’s most iconic works and then poignantly lingers over Georges Seurat’s “A Sunday on La Grande Jatte” — its pointillist style (a montage of tiny dots) serving as a reflection of Frye’s teen angst and neurosis. It’s still there in Gallery 240, and, in no small way thanks to the movie, it’s one of the Art Institute’s bingo cards. During the coronavirus pandemic, the 19th-century masterwork also appeared in one of the lighthearted “Where’s Lightfoot?” memes showing Chicago’s mayor keeping watch over the city during the lockdown.

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Nearly four decades later, the museum’s content remains constant, with perennial blockbusters such as Grant Wood’s “American Gothic,” Edward Hopper’s “Nighthawks” and Marc Chagall’s enchanting “America Windows.” Whether visitors want to relive in rote form a slice of ’80s nostalgia, be part of digital folklore or are genuinely perplexed and moved like Frye, “A Sunday on La Grand Jatte” remains a major crowdpleaser.

What has changed, though, is the addition of the stunning Renzo Piano-designed Modern Wing, which showcases 20th- and 21st-century art. It’s best approached on Frank Gehry’s serpentine pedestrian bridge, which connects the museum to Millennium Park. The dazzling new wing showcases works by contemporary masters such as Pablo Picasso, Henri Matisse, Willem de Kooning and Jackson Pollock, whose “action painting” technique deployed in “Greyed Rainbow” transfixed these three particular teens.

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Related: 11 must-do activities when visiting Chicago

Millennium Park: ‘The question is, what aren’t we going to do?’

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In the age of social media, no Chicago visit is complete without a selfie in front of “The Bean.” Just north of the Art Institute, Anish Kapoor’s “Cloud Gate” sculpture (as it’s officially known) is everything a public space should be and invites real interaction — and an opportunity to share online that’s rarely wasted by Generation Z.

With Chicago’s skyline captured in its shiny, fun house reflective surface, the beloved legume forms the centerpiece of Millennium Park, which opened after a budget-blowing controversy in 2004. Framed by Chicago’s soaring cityscape to the west and Lake Michigan to the east, there are monumental feats of art and engineering — notably, Frank Gehry’s postmodern Jay Pritzker Pavilion — and the 3-acre Maggie Daley Park, which features themed play areas, a 40-foot climbing wall, miniature golf and a skating ribbon.

If Bueller were playing hooky in 2022, surely this would be his playground. The city and the skyline have evolved, but teens really haven’t. This constant urge to connect and share with friends in real time throughout the day was the whole reason Bueller played hooky in the first place.

Related: 8 things to do in Chicago with kids

Wrigley Field: ‘Right now we’d be in gym’

One of America’s most beloved ballparks, ivy-covered Wrigley Field has been the home of the Chicago Cubs for more than 108 years. Midwestern loyalty, pride and authenticity fill the air, and the long-standing traditions that keep the ballpark so special remain intact — the manually operated scoreboard was retro even when Wrigley played a staring role in “Ferris Bueller’s Day Off” and cameoed in “The Blues Brothers.”

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There are still few better ways to play hooky anywhere, anytime, than to watch a game at Wrigley, eat hot dogs (Chicago style, of course) and sing “Take Me Out to the Ball Game” during the seventh-inning stretch, a tradition coined by the late broadcaster Harry Caray.

Since the day when Bueller and Frye watched the Cubs lose 3-2 to the Atlanta Braves on June 5, 1985, according to Larry Granillo of baseball blog Wezen-Ball, the stadium has undergone a massive restoration, adding more modern comforts and amenities while still retaining its old-fashioned charm. The fierce loyalty of sport-obsessed Chicagoans was finally rewarded in 2016 when the Cubs won their first World Series in more than a century.

Ticket prices depend on how the Cubs are performing, but expect to pay around $30 per ticket. You can also sign up for tours that visit the press box, clubhouses, bleachers and team dugouts.

Related: Check me in to the ballgame: 10 great baseball stadium hotels

Von Steuben Day: ‘We’d like to play a little tune for you’

With a packed calendar of festivals and events that celebrate the city’s rich cultural tapestry, Chicago knows how to throw a great party.

In the early 20th century, immigrants from Eastern Europe, Mexico, Italy, Greece and Germany flocked to Chicago, leaving their mark on the city’s downtown, neighborhoods and street festivals — Chicago even dyes its river green in honor of St. Patrick’s Day.

Hijacking Chicago’s Von Steuben parade is one of Bueller’s most audacious and memorable acts. Jumping on a parade float to croon “Danke Schoen” and then inspire a joyous “Twist and Shout” flash mob at the epicenter of downtown Chicago is part of city lore, but it would be impossible today with increased security post 9/11.

As Chicago’s Oktoberfest traditions have evolved, celebrations now take place some 5 miles north in Lincoln Square, a vibrant neighborhood known for its tree-lined streets, distinct German traditions, craft beer, community art projects and diverse restaurants.

But why does the city don lederhosen and toast the Prussian Baron Friedrich Wilhelm von Steuben in the first place? It was Baron von Steuben, “the father of the U.S. military,” who was responsible for transforming the Revolutionary War army into a disciplined fighting force, according to various sources (or whoever you ask at the Dank Haus in Lincoln Square).

Held the second weekend in September, Oktoberfest is a joyful way to wrap up summer in Chicago. The lively street party takes place under two huge tents and involves drinking beer from plastic steins, German delicacies, oompah music, fun games and overall merriment. 

Related: Prost! Here are the best places to celebrate Oktoberfest in America

Federal Plaza: Less is more

Another famous “Ferris Bueller’s Day Off” backdrop, Federal Plaza was the brainchild of legendary German Ludwig Mies van der Rohe.

The father of American modernist architecture, Mies van der Rohe’s “skin and bones” constructions have become signature parts of the Chicago skyline.

Fans of the International Style will swoon for Federal Plaza’s load of pure Miesian austerity: The Everett McKinley Dirksen U.S. Courthouse, the low-slung John C. Kluczynski Federal Building (which houses a post office) and the Ralph H. Metcalfe Federal Building are just a few plaza standouts. Anchoring the square, Alexander Calder’s brilliant red “Flamingo” stabile has become one of Chicago’s storied symbols.

There’s always been a lot of love for mold-breakers like Calder in Chicago. The American sculptor was honored with his very own Alexander Calder Day on Oct. 25, 1974, a celebration that involved marching bands and circus wagons, and featured Calder himself as the ringmaster, holding court atop a Schlitz beer wagon. It’s the kind of extravaganza you’ll only find in Chicago.

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Related: 11 architecturally spectacular wildlife lodges around the world

Daley Plaza: The Picasso slide

It was in the ’80s that Chicago become one of the U.S.’s most coveted filming locations. John Belushi famously offered then-Mayor Jane Byrne a donation of $200,000 to a local orphanage to film “The Blues Brothers” in Chicago, and then he piled on the wreckage in outrageous fashion.

The film’s famous demolition derby, which took place on Lake and LaSalle streets, held the record for the most cars destroyed (105) during a movie production. The mantle was passed to “Transformers: Dark of the Moon” in 2011 (also filmed in Chicago) when 523 cars were destroyed. 

Sign up for a movie tour today and you’ll hear the anecdotes behind one of movie history’s most memorable scenes: the Bluesmobile smashing into the Richard J. Daley Center as cops and soldiers engulf the square — Mayor Jane Byrne, who wasn’t a fan of one of her predecessors, the building’s namesake, apparently enjoyed the symbolism.

For Chicagoans, Daley Plaza is the setting for the Christkindlmarket, the city’s longest-running farmers market, and one of its most emblematic sculptures: Picasso’s 50-foot-tall, 162-ton nameless sculpture.

When the sculpture was unveiled in 1967, controversy raged over what public art should represent. What is it? An Afghan hound, a strange bird or “the pelvic structure of a prehistoric monster,” as a bystander told legendary Chicago writer Studs Terkel? Not long after the sculpture was installed, kids started using it as a slide, and so began the city’s passion for interactive sculptures.

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Related: From Philly to Chicago, here are 6 of our favorite US Christmas markets

Bottom line

From art and architecture to theater and music, Chicago has a knack for rewriting the book. The city’s dynamism and powers of reinvention account for its consistent ranking as “the best city in America” in reader polls and travel publications.

Certainly, themed movie tours and immersive ’80s exhibitions offer a fun slice of nostalgia and help connect the dots; The ’80s gave us the first Taste of Chicago festival and the first Black mayor (Harold Washington), and no Chicagoan alive in the ’80s can forget “Spider Dan” climbing Sears Tower or the citywide euphoria when the Chicago Bears won the Super Bowl in ’86.

However, teen dreams are different today. A deep-dish pizza or an Italian beef sandwich would always trump haute cuisine at Chez Quis, which, unlike most of the movie’s other locations, never existed. Given absolute freedom from authority for the day, a visit to Chicago’s Board of Trade would rarely rank high on a Gen Z teen’s freewheeling agenda.

Bueller is said to have everything a teenager needs to know, and Chicago is everything a 21st-century metropolis should be. While teens will always crave excitement and independence, their avenues in 2022 are very different from those available 35 years ago.

Still, one thing’s for sure: On every block and behind random doorways in Chicago, there’s always a story — you just don’t need to stick to one script.