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A Ferris Bueller-inspired Escape to Chicago

Life is short. If you don’t stop to look around once in awhile, you may just miss it,” exhorted Matthew Broderick in his starring role in the 1986 classic film Ferris Bueller’s Day Off, in which three high schoolers skip class to enjoy a beautiful spring day in the city. As a teen working part-time at National Video, I’d pop that VHS tape into the VCR every chance I got. Ferris was a hero to me, and many other Gen-Xers; and the movie was an inspiration to seize the day, escape the boredom of school, and do whatever you needed to have fun.

And after visiting Chicago 32 years later, I have to say he was right to play hooky (don’t tell my kids I said that). It’s a fabulous city. So take a few days off to enjoy Chicago’s best sights à la Ferris.

Skydeck Chicago

Skydeck Chicago

The Ledge at Skydeck Chicago wasn’t around when Ferris Bueller took his famous day off school, and that may have been a good thing! (Photo courtesy of Skydeck Chicago)

Sloane: The city looks so peaceful from up here.
Ferris: Anything looks peaceful from one-thousand, three-hundred and fifty-three feet.
: I think I see my dad.

Pressing their heads against the glass, the main characters took in the view of Chicago from the top of Sears Tower (now called Willis Tower). If the three truants were here now, they’d probably be striking Instagram-worthy poses on the Ledge at Skydeck, a heart-stopping glass balcony 4.3 feet outside the buildings.

“Ferris was the influence for the edge,” said general manager Randy Stancik. Hugely popular, the attraction sees on average 4,700 people a day, and there have been more than 100 marriage proposals on the ledge. No doubt, Ferris would have loved it.

Art Institute of Chicago


You just may fall in love with the Art Institute of Chicago, just as the characters in “Ferris Bueller’s Day Off” did. (Jennifer Merrick photo for VacayNetwork.com)

Cameron fell into a trance when he looked deep into one of the museum’s most famous paintings — A Sunday Afternoon on the Island of La Grande Jatte by Georges Seurat. This captivating museum houses the greatest Impressionist collection outside of Paris. It also spans the globe with galleries featuring art from Ancient Greece, Japan, Africa, and the Americas. Can’t-miss pieces include Vincent Van Gogh’s Self-Portrait, Grant Wood’s American Gothic, Edward Hopper’s Nighthawks and Marc Chagall’s America Windows (in front of which Sloane and Ferris share a romantic moment).

Wrigley Field


The Cubs play many of their home games during the day, enticing many teenagers like Ferris to skip school in order to catch some baseball action. (Jennifer Merrick photo for VacayNetwork.com)

“Hey batter, batter, batter! Swing batter!” Cameron chanted when they caught a baseball game and a foul ball at this much-loved Chicago stadium and landmark. See a game or take a tour of the home of the Chicago Cubs, where some of the most memorable moments in the history of baseball have been played.

Where to Enjoy Chicago’s Dining Scene

Maitre d’: You’re Abe Froman?
Ferris: That’s right, I’m Abe Froman.
Maitre d’: The Sausage King of Chicago?
Ferris: Uh yeah, that’s me.

Though the fancy restaurant Ferris bluffs his way into was fictional, a day off in Chicago would not be complete without an unforgettable meal or two or three or … a dozen. Cuisine in the city is legendary, earning numerous accolades, so there are plenty of options. Beatnik Restaurant is dazzling both in its decor with 15 massive chandeliers salvaged from a ballroom and in its delicious food with a Middle Eastern slant. Tortoise Supper Club, with its stately decor, looks as if it’s been around for at least 100 years, but in fact, it opened in 2012. The food is sophisticated and tasty, and unlike Ferris’s experience, the waiters are friendly and not at “snooty” or “snotty” as Bueller would say.  Speaking of unpretentious, Band of Bohemia is a brewpub with a difference and that distinction is a Michelin star. Dishes like dry-aged beef and crispy pork belly can be paired with wine or beer brewed on the premises. For brunch you can’t go wrong with The Dearborn Tavern that serves up Chicago favorites with a twist in a bright yet cozy atmosphere (Tip: try the crab Benedict).

Even the food courts serve up top-notch cuisine. The Chicago French Market has 30 individual speciality vendors, including Aloha Poke Co., which opened its first Hawaiian eatery in the market, and Pastoral for artisan cheese, bread, and wine. At the Revival Food Hall in the heart of the business district there are 15 outposts of Chicago-based neighborhood restaurants, including the Furious Spoon, famous for ramen, Smoque BBQ, Antique Taco Chiquito, and Hot Chocolate Bakery.

Unfortunately, Ferris and his buddies were too young to imbibe as Chicago’s cocktail scene is also thriving with hideaways and hidden gems like a fully stocked mezcal bar at Quiote, amaro flights at Billy Sunday, and cocktails with a view at Robey Hotel’s rooftop bar in the hip Wicker Park neighborhood. If you don’t stop to look around though, you may just miss them.

And life is short so take some time off to enjoy the Windy City.


Chicago CityPASS: Skip the lineups and save money with this all-in-one pass. The prepaid admission includes entry to Ferris-related attractions like Museum of Science and Industry, Skydeck Chicago, Shedd Aquarium, Field Museum, Adler Planetarium, and the Art Institute of Chicago. Cost is $151.40 for adults, a savings of 50 percent on premium admissions.

Ventra Card: Getting around Chicago on public transit is convenient and easy. A three-day Ventra card gives unlimited access to subway ‘El’ trains and busses. Cost is $20 and available from any Ventra Vending Machine.

Four Seasons Hotel Chicago: Ferris would have loved staying at this luxurious hotel with its five-star service and amenities. Located downtown near the Magnificent Mile it rises high above the city providing gorgeous views of the city skyline and Lake Michigan. A recent search of the hotel’s online booking engine returned a nightly rate of $383 for a weekend stay in May.

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