Chicagoland: Gateway to the West

“I’ve hit Chicago, but Chicagoland? Never. That alone made this leg of the journey even more enticing, a perfect way to kick things off.

Not that we needed enticing.

Remember your first day of school? Work? Summer camp? The eagerness. The excitement. That urge to dive in headfirst. Optimism bubbling up. Anything feels possible.

Now, imagine embarking on a long vacation. Same vibe. That first-day buzz. All that anxiety while you crammed your suitcases? Poof! Gone!

It’s dawn. The sun bathes the trees in a warm morning glow. You’ve got that road trip energy. You practically leap into the driver’s seat. And when the tires finally start rolling, whatever remaining burden sitting on your shoulders floats away, as if an invisible fence forbids it from leaving the driveway with you.

You’re free. After years of dreaming, it’s westward ho!

Three days of our trek were mostly on the road. This was one. Long hours, long road ahead. But it’s Day One! Nothing could get us down. Even our much-anticipated “first stop” at the newly reopened Angola Thruway service area? No disappointment.

By rights, it should have.

We looked forward to a Shake Shack breakfast and a delicious cinnamon roll from Cinnabon. Unfortunately, our eagerness to leave early meant we arrived way before opening. Oh well. Put us back on the road quicker.

Perfect! We had only just started, and we were already ahead of schedule. Peter and Catarina had plotted our itinerary with the precision of a guided missile. Throughout our ten-day journey, we’d know exactly our position and our time. In a skewed way, they seemed to have outwitted Heisenberg. (Yes, I know Heisenberg paired position with momentum and time with energy, but I did say “in a skewed way.”)

This portion of I-90 had us tooling along familiar terrain. Well, at least we were tooling along until we noticed dark smoke up ahead. It was a Jeep. On fire. Apparently, since the road had only just started to get clogged, the event had just occurred. We detected the hazard at the last moment and pulled off the exit for a short detour.

And that, my friends, is how Michigan appeared unexpectedly on Catarina and Peter’s meticulously crafted itinerary. That put us slightly behind. No worries. It could have been worse. It could have been raining.

And then it started to rain. A drizzle at first. Then buckets. Just in time for our stop in South Bend, Indiana, and our meeting with “Touchdown Jesus.”

I can’t really describe, let alone explain, the widespread appeal of Notre Dame University. You don’t have to be a Catholic to adore the Fighting Irish. It’s just one of those things. An American thing, maybe. After all—Knute Rockne, George Gipp—what could be more American?

Water-soaked skies? We didn’t flinch. Not even once.  A soggy lap around Notre Dame’s stadium? Done. We ducked into the bookstore, snagging Irish gear—including a lanyard for our rented Expedition’s key, naturally. (Wet shoes, epic haul, right?)

Isn’t it odd how the pouring rain can make any experience more unforgettable? It’s these random things that become lifelong memories on any family outing.

No time to linger—the schedule was calling. I grabbed the wheel, dodging Chicago’s heart for its western burbs. Destination: my first-ever friend from Abbott Parkway. (Three years old, building snow forts, playing house—wild, huh?) Time’s a funny thief, stealing decades but leaving memories untouched.

I hadn’t seen her in more than fifty years. Her daughter found me on the internet after I appeared on Chicago radio to talk about the origin of the hamburger. We’d been email pen pals since, so we had a chance to get reacquainted.

Our families? Not so much. We had each told stories about each other to them, so their expectations were… unknown. But people are people, and growing up together, no matter how many years separate you, creates inseparable commonalities. Traits invariably pass down.

And so it was in this case. Whatever trepidation existed at first quickly evaporated. Curiosity proved far too compelling, overpowering any initial wariness.

Soon, laughter filled the dinner table. Shared memories flowed like wine, or in my case, Diet Pepsi. (Wine’s overrated, trust me.) Half-century-old tales retold (and reinforced). New bonds sparked. Our families meshed fast.

For my old neighbor and me, it was like stepping out of our legends. No longer fictional characters, the visit transformed us into real, flesh-and-blood people.

Plus, different (but corroborative!) perspectives on the same stories? Priceless.

We left way too early, but the midnight hotel check-in loomed (something like the Expedition turning into a pumpkin). And Chicago was an hour away.

The next morning kicked off bright and early (a theme that would repeat itself) as we began our walking tour.

They call Chicago “the Second City” (after New York City). While it doesn’t have quite the skyline, for decades it boasted the world’s tallest building: the Willis Tower (née Sears Tower). It surpassed New York’s original World Trade Center towers and held the title until 1996. Like the CN Tower in Toronto, the Willis Tower features a protruding glass-encased observation deck. You can walk out and peer 100+ stories below.

Notice I said “you.” Me? Never. Wouldn’t even venture up that high. Such is life with me and heights. The rest of the family, though? Up they went! I stayed ground level, phone in hand, watching a confident baker ready the strangely named Do-Rite Donuts & Chicken shop.

Turns out Catarina was the only one brave enough for the “thin air.” (The air outside wasn’t that thin; it was thick with fog.) Top of the building? Hidden by low clouds. On the 103rd-floor Skydeck, if Catarina had mimicked Ferris Bueller, leaning against the glass to look down, she’d have seen nothing but cloud. There was no sense of height.

Catch that? See how Chicago becomes Chicagoland?

Now, for you purists, “Chicagoland” refers to the Chicago metropolitan area. But here? It’s a play on words, as in “Hollywoodland.” Alluding to all those famous films featuring very viewable Chicago landmarks.

Cesidia started the ball rolling, mapping John Hughes’ filmmaking haunts in or near the Windy City. We tossed in more films, brainstorming fast. (Got a little carried away, truth be told.) Before Willis Tower, we swung by the parking garage from Ferris Bueller’s Day Off. Cameron’s red 1961 Ferrari 250 GT California Spyder sat there in spirit. Yes, we hummed the Star Wars theme, grinning as we walked by.

Willis Tower done, we hit Union Station. Deserted. Weekend dawn hush. Perfect for snapping that staircase. You know the one. The Untouchables. Pure cinematic gold. The fiery shootout. Kevin Costner’s Eliot Ness and his men take on Robert De Niro’s Al Capone and his boys. Baby carriage? Remember that?

What you might not remember? That staircase scene? A remake! Brian De Palma’s 1987 movie paid homage to the “Odessa Steps” scene from the 1925 Soviet silent classic The Battleship Potemkin. Propaganda as art? Maybe. (Chicago’s raw edge trumps it, though.) The Untouchables steals the show. Chicagoland’s a reel, folks. A reel for Ness. A reel for us.

Back to Ferris Bueller. We hoofed it to the Chicago Board of Trade. No entry—Saturday, no trading. (No mocking traders like Ferris, sorry.) For those keeping score at home, the building also snagged an exterior shot in The Untouchables.

Speaking of exterior shots, the Federal Center (our next stop) lurked in the background of The Blues Brothers’ downtown chase. But there’s a better location for that film.

Jake and Elwood? Daley Plaza’s non-negotiable. Their tax sprint to the Cook County Assessor’s Office. (Spielberg’s cameo as the clerk in that scene!) We wandered through. No army this time. Just a few cops, eyeballing a lackluster protest.

Too early for the art museum, so we lingered at Millennium Park’s Bean. Gleaming. Mirrored. Selfie haven. Interesting enough to appear in more recent motion pictures like Source Code and Transformers. Didn’t go there for that. Just had to kill time. And maybe get a Christmas Card pic.

A special pass let us zip past the waiting line into the Art Institute of Chicago. Beelined for Gallery 240, Impressionism room. It’s the location of Seurat’s A Sunday Afternoon on the Island of La Grande Jatte. That painting famously drew a tear from Cameron’s eye in Ferris Bueller’s Day Off. Sure, other masterpieces beckoned (American Gothic, Nighthawks, and a cool desk designed by Frank Lloyd Wright). But this is what we (and many others) came to see.

Chicagoland’s highlight, both figuratively and literally, had to be the driving tour outside the city limits. After hot dogs at Portillo’s, we drove to the former Maine North High School in Des Plaines. Now a police station. In 1985, it starred as the high school in The Breakfast Club.

Then, Glenbrook North High School, 2300 Shermer Road, Northbrook. John Hughes’ real-life alma mater. In ‘86, it played Ferris Bueller’s high school. The stairs where Ferris picked up Sloane? Right there for you to see. In the back? The football field where Judd Nelson defiantly marched off at the end of The Breakfast Club.

It’s only a quick hop to the Northbrook water tower, famous for the large “Save Ferris” painted on it for the movie. Was it our imagination, or could we see the ghost of those letters still faintly on the tower?

The clock, that sneaky usher, pushed us on. Long day. We were city-bound for a much-deserved hearty meal at Italian Village. Still, time for a quick stop at Glencoe Union Church in—you guessed it—Glencoe, Illinois. This church hosted the wedding scene in Sixteen Candles.

Last stop: 671 Lincoln Avenue, Winnetka. That would have been the McCallister’s residence in 1990’s Home Alone. Tourists swarmed the street like bees to honey. (Pity the owners, right?)

And looking at that house, all I could hear was Catherine O’Hara’s plaintive cry, “KEVIN!”

The Italian Village stashed us into a tiny cubbyhole. Literally dug out of the wall. Barely big enough to hold the whole Carosa clan. The food came with such promise. Big servings. But, gotta be honest, Ilio’s sauce tops them. Still, we ate our pasta knowing we were headed straight into beef country. Next week would be nothing but burgers, steak, and—if we arrived in time—brisket.

Early the following morning, we hurriedly grabbed our luggage and rushed down to check out. Into the car, starting our 14-hour drive to Rapid City, South Dakota. Peter, firm at the wheel. Now, we were on roads only he had seen.

The rest of us settled in, getting comfy. Betsy and I shared the back seat. Strange. It felt roomier than usual. We exchanged puzzled looks. Something was missing. What? Then Betsy’s eyes lit up in surprise.

“CESIDIA!” she cried.

We’d left our eldest child alone in Chicago.