A fair share of great movies take place in the greater Chicago area. There are action classics like “the Untouchables” and “the Fugitive,” holiday favorites like “Home Alone” and “Christmas Vacation,” and feel-good rom-coms like “While You Were Sleeping” and “High Fidelity.” There’s “Mean Girls” and “Bad Moms,” “Eight Men Out” and “Sixteen Candles,” “My Big Fat Greek Wedding” and “My Best Friend’s Wedding” — heck, there’s even “Chicago.”

But one of the best remains the 1986 comedy “Ferris Bueller’s Day Off.” It’s the classic chronicle of the cocky Chicago teenager, his over-serious best friend Cameron, and his eccentric girlfriend Sloane as they skip school and take on the Windy City for the day. In the spirit of the fourth-wall-breaking Ferris, we’ve thrown together our own guide that you can use if you’ve got a free day to explore Chicago. To form your itinerary, simply pick one of the three options under each section — you’ll recognize a couple of the spots from Ferris’s own schedule, but for the most part, these are all new suggestions.

Breakfast

Lou Mitchell’s

There’s an old Greek tradition that dictates that you should offer something sweet to anyone you welcome into your home. That’s why everyone who walks into this classic Greek diner in Chicago’s Loop district is handed a couple of donut holes — and women and children are also gifted some Milk Duds. Despite it Greek roots, however, Lou Mitchell’s is definitively American. It’s even on the National Register of Historic Places, due to its unique position as the first restaurant on Route 66. Hospitality is the name of the game here, so whether you’re a first-time visitor or a Sunday-morning regular, prepare to be greeted with smiles and pet names — oh, yeah, and a stack of delicious pancakes.

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Chicago Bagel Authority

Anyone who’s ever visited Miami University — the brick-and-ivy liberal arts college tucked away in the small town of Oxford, Ohio — is familiar with the school’s true claim to fame: Bagel & Deli. The single-room hotspot is popular among both hard-studying double-majors and 2 a.m. stumblers, all of whom step up to its counter to order one of the menu’s 90-plus steamed bagel sandwiches, which are wrapped in tin foil and dripping with grease. What most people don’t know, however, is that a Miami grad modeled their Chicago shop, the Chicago Bagel Authority, after the popular breakfast spot, so any Miami alumnus in the city’s Lincoln Park or Lakeview neighborhoods can pick up one of their old favorites, such as the “Dank ‘N’ Eggs” or the “Hangover Helper.” Overwhelmed by your options? You can always start with something simple, like “Sam’s Sunrise” (scrambled eggs and American cheese on an egg bagel), and work your way up to one of the more complex offerings, like the “Belmont” (maple sausage, smoked ham, chive cream cheese, jalapeños, scrambled eggs, pepper jack cheese, and gouda on an everything bagel).

The Bongo Room

What you have for breakfast can really make or break how your entire day pans out. That’s why eating a hearty meal when you wake up is so important. But, sometimes, you want dessert first — and that’s okay. If you’re looking to indulge your morning sweet tooth, the Bongo Room is the place to be. The “sweet” half of its menu is loaded with confectionary concoctions that sound like something a kindergartner might dream up if told “you can have anything you want.” Favorites include white-chocolate and caramel pretzel pancakes, gingerbread and caramelized pear pancakes, and apple churro French toast. If this all sounds a little too sickeningly sweet, don’t worry. The “savory” side of the menu offers some great selections as well, from an egg-white reuben omelette to a vegetarian croissant sandwich.

Morning Activity

Architectural River Cruise

Ever since the introduction of the White City at the 1893 World’s Fair, Chicago has been recognized as one of the most interesting architectural metropolises on the planet. This is good news for tourists, as it means that any walkabout through the city’s streets will turn into a museum-like meander through its own exhibit of towering skyscrapers and Neo-classical design. But one of the most interesting ways to marvel at the city’s varied architectural wonders is from the water. Through Viator, you can book a 90-minute cruise that will float you down the Chicago River and past all of the buildings, piers, and cityscapes that make Chi-Town so beautiful. Along the way, you’ll pass by over 50 different skyscrapers, including the Sears Tower, the John Hancock building, and Trump Tower — the latter of which is much smaller than you may have been led to believe. With guided narration and complimentary snacks, this tour truly is the full package.

Garfield Park Conservatory

Even the most stunning cities can start to feel a little overwhelming at times, and often the best cure for gridlock-induced claustrophobia is a little escape into nature. In Chicago, the most spectacular spot for that is the Garfield Park Conservatory. This breathtaking botanical area offers two acres of greenhouse gardens (often referred to as “landscape art under glass”) and 10 acres of outdoor natural spaces, which feature refreshing flora, a water lily pond, and a seemingly neverending escape from the bustle of the city. Oh, and did we mention it’s free?

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Lakefront Trail

You might assume that visiting a big city like Chicago means leaving your running shoes or roller blades at home… Well, think again! The Chicago Lakefront Trail is a natural scenic path hidden within the urban jungle. This 18-mile trail stretches along the stunning coastline, from Ardmore on the North Side to 71st street on the South Side, providing a beautiful path for walkers, joggers, cyclers, and bladers. If you want to take a day to attempt the entire thing, feel free, but we recommend spending your morning tackling a four- or five-mile stretch. You can also hop on a Divvy bike (the city’s bike-share program) to traverse the path. Along the way, you’ll be treated to unbelievable views of the deep blue expanse that is Lake Michigan.

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Lunch

Manny’s

Need convincing that this Jewish deli on the South Side is a favorite among Chicagoans? Just take a look at the walls, which are decorated with news clippings, memorabilia, photographs, and other testaments to just how much the city’s residents treasure this spot. Having first opened its doors during World War II, Manny’s Cafeteria and Delicatessen has been serving up its signature corned beef and pastrami sandwiches for over 75 years now — and it’s showing no sign of slowing down. Still not convinced you’re going to enjoy stopping in for lunch? Just take it from one fairly notable Chicagoan.

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Publican

Fittingly situated in Chicago’s meatpacking district, Publican Quality Meats is part butcher shop, part gourmet market, and part café — in other words, whatever you’re craving, you can probably find it here. From chicken-parm sandwiches to freshly baked bread, craft beer and wine, and house-made charcuterie, the market offers an ever-growing menu of delectable options. Whether you want to grab an espresso to help you power you through to dinner or you’d prefer to chow down on their (very-filling) spring chicken sandwich, Publican is your one-stop shop.

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Pequod

Asking for thin-crust pizza in Chicago is akin to sporting a tank top at the Vatican. So, if flatbreads are your thing, maybe stick to sausage during your stay in the Windy City. If you’re game to dig in to some deep dish, however, the question becomes, Where should I start? Deep-dish pizza joints are so prevalent throughout the city that you’ll never need to worry about missing out, but with so many choices, it can be difficult to figure out where to get the maximum hometown experience. While Pequod might not serve up the most classic Chicago deep-dish, it does offer one of the tastiest — and one of the cheapest. For just $4.95, you can grab a fountain soda and a personal cheese pie with the pizzeria’s famous caramelized crust. But for the full Chi-Town experience, we suggest splurging on some additional toppings — sausage and pepperoni, perhaps?

Afternoon Activity

Record Shopping

When you think of Chicago, you might picture sizzling sausages, zealous sports fans, and brilliant architecture — but don’t forget about the city’s vibrant music scene. From Chicago Blues and jazz, to the rock and house of the ’70s and ’80s, to the recent explosion of hip-hop and independent rap, Chicago has been at the forefront of the music world for the better part of the last century. So, what better way to spend an afternoon than by sampling some of the city’s auditory offerings? There are plenty of record shops to choose from throughout the city, but we recommend starting with the endless stacks at Reckless Records, the old-school atmosphere of Dave’s Records, or the indie paradise that is Laurie’s Planet of Sound.

The Art Institute of Chicago

While it’s the most Ferris Bueller destination on this list, the AIC is truly a must-visit for anyone who remotely considers themself a fan of good art. Even if you’re anti-art — whatever that means — a few hours at the Institute would still make for a mind-blowing afternoon. The sheer atmosphere of this museum is astounding, and you’re bound to find something you enjoy among the 300,000 works of art spread throughout its many rooms. And, for fans of the film that this article takes its inspiration from, the painting you’re looking for is called “A Sunday on La Grande Jette,” and it can be found in the Helen Birch Bartlett Memorial Collection.

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Second City

What do Tina Fey, Mike Myers, Dan Aykroyd, Amy Poehler, Jane Lynch, and Steve Carell all have in common? What about Bill Murray, Jordan Peele, Gilda Radner, John Candy, and Fred Willard? If you guessed that they’re all comedians, you’re… well, you’re technically right. But more specifically, they all got their starts at Second City, a world-famous improv school located right in Chicago’s Old Town neighborhood. For over 50 years, Second City has operated sort of like the Harvard of comedy (though the actual Harvard has produced its own fair share of comedians), churning out generation after generation of hilarious actors who went on to successful careers in film and TV. Today, you can still catch a show every day of the week. And, who knows — you just might spot the next big comic while you’re there!

Dinner

Band of Bohemia

Foodies visiting Chicago might be expecting to encounter more brewpubs than Michelin-starred restaurants. At Band of Bohemia, located on the city’s North Side, they’ll get both. Housed in a repurposed brick building and furnished with elegant seating options, the restaurant emits a mix of Victorian and industrial atmospheres, and the menu is equally diverse. Large stainless-steel tanks hold craft brews that are paired with the chef’s small- and large-plate offerings, both of which are sure to surprise both the eye and the palette. Due to Band of Bohemia’s deserved popularity, tables can be hard to come by, so if you want to dine here, be sure to make a reservation ahead of time.

Gibson’s

America’s meatiest city offers its fair share of steakhouses — but it’s hard to deny that Gibson’s is the best. The swanky eatery on North Rush Street is nothing short of iconic, a favorite among both locals and celebrities for its angus beef, fresh fish, refreshing libations, and white-jacket service. Named in Chicago Magazine’s “Best of Chicago” issue and honored as the best steakhouse in the city by a multitude of publications, Gibson’s is a quintessential Windy City experience. If you’re looking for a similarly classic Chicago eatery but think that Gibson’s pricier offerings will have you digging through your purse in search of runaway bills, walk three minutes north through Mariano Park and arrive at Lou Malnati’s, a local deep-dish favorite. Also, whichever restaurant you choose, walk off your dinner afterward with a half-mile stroll to Garrett’s Popcorn Shop, located in Water Tower Place. There’s no better Chicago dessert than some of Garrett’s classic cheddar-caramel mix.

Bang Bang

Granted, the pie shop responsible for initiating Chicago’s pie boom isn’t exactly a traditional dinner spot — the Ravenwood location closes at 4 p.m., and the Logan Square location only stays open until 7 p.m. Monday through Friday. But, if your day in the city happens to fall during the week, this spot should definitely be in the running for your dinner stop. Made famous by its delectable key lime pie, Bang Bang Pie Shop also serves up unforgettably savory biscuits and gravy, as well as other filling homestyle dishes like pot pie and grits. That, plus a steaming mug of post-meal coffee will be just the kick to carry you through your evening activity.

Evening Activity

Catch a game

Bulls, and Blackhawks, and Bears… oh my! Chicago is one of the rare places where sports teams are more than just niche fan clubs — they’re ingrained in the fabric of the city. If you live in Chicago, you don’t have to be a football fan to know that you’re supposed to hate the Green Bay Packers. And, whether or not you can explain what icing is, you know that if “Chelsea Dagger” is playing, your Blackhawks just scored a goal. For Chicagoans, fandom isn’t a choice; it comes with the territory. So, even if you can’t stand the city’s multitudes of bandwagon fans who come out of the woodwork whenever a Chicago team wins a championship, you owe it to yourself to make it to a game just to experience the unique atmosphere. If it’s a Sunday and the Bears are in town, that might be your best option, but otherwise head to Wrigley to see the Cubs (formerly known as the Lovable Losers), the United Center for a Bulls or Blackhawks game, or Guaranteed Rate Field to see the Cubbies’ crosstown rivals, the Chicago White Sox.

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Enjoy the Music

As we’ve mentioned several times, the music scene in Chicago is hard to beat. So why not spend the night enjoying some Windy City beats? If you’re looking to hit the dance floor, opt for the Empty Bottle, a down-and-dirty hole-in-the-wall featuring indie and alternative bands every night of the week. A killer spot for those in search of cheap drinks, lively music, and an unbeatable atmosphere, the Empty Spot is truly a classic Chicago club. If you’d prefer something a little smoother, head to the Green Mill, a smoky jazz lounge nestled at Lawrence and Broadway. In business since 1907 (when it was named Pop Morse’s Roadhouse), the Green Mill offers a variety of soulful performances — from Monday evenings with the Chicago Jazz Orchestra to Saturday night “After Hours” shows that last until 5 in the morning and Uptown Poetry Slams every Sunday night. Steeped in rich history and renowned for its tradition of excellence, the Green Mill remains one of the most popular venues in town.

Take in a Show… or 30

If you don’t like what you’re seeing during “the Infinite Wrench,” a production by Chicago’s experimental theatre ensemble the Neo-Futurists, then just wait a bit. The performance will be over in a minute or two — and then a new one will take its place. The rules of “the Infinite Wrench” are simple: based on “Too Much Light Makes the Baby Go Blind” (which the troupe performed for 28 years until the director rescinded its right to use his trademarks), the performance unleashes a cavalcade of short performances upon the audience, attempting to fit 30 one-acts into 60 minutes. The ever-changing plays, which are written and developed by the ensemble in the week leading up to the performance, range from hilarious to depressing to elegant to profound. You never know what you’re going to get — and just when you’ve figured it out, the next play will have begun.

Of course, you don’t have to limit yourself to what you choose here; think of this more as a starting point. Whatever you end up doing during your day off, just be sure to take a moment to enjoy it. As Ferris says, “Life moves pretty fast. If you don’t stop and look around once in a while, you could miss it.”

Cover Photo by Tim Trad

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Devon Shuman
Devon Shuman is a creator, a storyteller, and a traveler from Boston, Massachusetts. He caught the travel bug at a young age when his family would take camping trips in southern Maine and New York’s Adirondack region. Since then, his adventures have taken him all across the globe. His favorite journeys include island hopping in the Galápagos, thru-hiking Vermont’s Long Trail, and summiting Mount Kilimanjaro. He currently works as an editorial consultant for Passion Passport, helping explorers from around the world tell their stories.