Let's Take a Day Trip

CHICAGO — There’s hardly a day that goes by when I’m not sitting in front of my laptop with Google Flights open, trying to figure out where I’m going next.

I’m constantly comparing airfare to Montreal, checking flights to Calgary, wondering if I can squeeze in another weekend in New York, or daydreaming about walking the streets of Santa Clarita, California. Planning the next trip has become part of who I am. Sometimes I think I enjoy researching the adventure almost as much as taking it.

Over the weekend, my older brother Jared asked me a simple question that completely changed my perspective.

“On a beautiful day like today, why don’t you just go to downtown Chicago and explore?”

At first, I brushed it off.

Jared and I both live in Illinois, but our lives look very different. He lives in Peoria, a midsize city about three hours southwest of Chicago. Whenever I visit him, I enjoy spending time at Par-A-Dice Casino, watching my son run around with his cousins, and taking in the peaceful views along the Illinois River in nearby East Peoria. Life there moves at a slower pace. It feels relaxed, comfortable, and uncomplicated.

My life in Chicagoland is much more routine.

I live in the same south suburban community where I work. If I wanted to, I could walk from my front door to my office in about ten minutes. During the school year, my son’s school bus stops directly outside our house. Most days follow the same rhythm.

Ironically, despite living just outside one of the world’s greatest cities, I rarely visit it.

Unless I’m helping one of the older members of my family with an appointment or errand, I usually avoid downtown Chicago altogether. I don’t enjoy fighting traffic. I don’t enjoy searching for parking. Somewhere along the way, I convinced myself that if I wanted an adventure, I had to board an airplane.

Getting a pedicure somehow felt more exciting in Southern California.

Shopping at Macy’s seemed more special in Midtown Manhattan.

Walking through neighborhoods felt more meaningful in Toronto than it ever could in Chicago.

At least, that’s what I told myself.

So I accepted my brother’s challenge.

I drove north from the south suburbs along Interstate 94—the Dan Ryan Expressway—and parked near Roosevelt Road and Canal Street, just southwest of downtown. After grabbing a bottle of PATH water from Whole Foods, I started walking east.

As I crossed the Roosevelt Road Bridge, everything around me seemed to slow down.

Beneath the bridge stretched dozens of railroad tracks leading into Chicago’s historic Union Station. Freight trains and commuter trains crisscrossed below like veins feeding the heart of the city. To my left, the Chicago River quietly wound its way through towering buildings of glass, steel, and concrete.

Then I looked up.

Standing before me was the Sears Tower.

Officially it’s called Willis Tower today, but to many Chicagoans—including me—it will always be the Sears Tower.

Its dark, towering silhouette rose high above the rest of the skyline, surrounded by skyscrapers that reflected the afternoon sun like mirrors. It wasn’t just another building.

It was a reminder.

I stopped walking.

For a few moments, I simply stood there, taking it all in.

And then something happened that I wasn’t expecting.

I fell in love with Chicago all over again.

As a kid growing up, I was fascinated by this skyline.

I would dump buckets of LEGO bricks onto the floor and spend hours trying to recreate Chicago’s skyscrapers from memory. The Sears Tower was always the centerpiece. No matter how many cities I’ve visited over the years, I still believe Chicago has the greatest skyline in the world.

But somewhere along adulthood, I stopped seeing it.

It had become ordinary simply because it was familiar.

I spend so much time chasing experiences in other cities that I forgot to appreciate the extraordinary place that’s been in my own backyard all along.

Chicago isn’t just downtown.

It’s neighborhoods full of personality and history.

It’s Hyde Park, where beautiful architecture, museums, and lakefront parks tell the story of the city’s South Side.

It’s the West Loop, where former warehouses have become some of the country’s most celebrated restaurants.

It’s Southport Corridor in the Lakeview neighborhood, one of my favorite places to spend an afternoon walking among local shops, cafés, and tree-lined streets.

Every neighborhood offers a different version of Chicago.

Every block tells a different story.

As I continued my walk, I realized something much bigger than whether or not I should visit downtown more often.

The places I spend thousands of miles flying to aren’t necessarily better.

They’re simply different.

The walkability I admire in Montreal.

The beautiful public spaces I enjoy in Calgary.

The neighborhood charm I love discovering in Southern California.

The feeling of wandering without an itinerary.

Many of those same experiences exist less than an hour from my front door.

Somewhere along the way, I had convinced myself that adventure required a boarding pass.

That if I wasn’t collecting airline miles or checking into a hotel, somehow the experience didn’t count.

But standing on that bridge overlooking the city that helped shape me, I realized adventure isn’t always about going farther.

Sometimes it’s about seeing familiar places through unfamiliar eyes.

That was my full-circle moment.

As a child, Chicago inspired my imagination.

As an adult, I overlooked it while searching for inspiration elsewhere.

Walking through the city reminded me that the place that first made me dream about exploring the world still has plenty left to show me.

Will I stop traveling to Montreal, Calgary, Edmonton, New York, or Santa Clarita?

Absolutely not.

Travel will always be one of my greatest passions.

But my definition of travel has changed.

Sometimes the best journey doesn’t require TSA, a passport, or even an overnight bag.

Sometimes all it takes is listening to your brother, driving thirty miles up the expressway, crossing a bridge, and remembering why you fell in love with home in the first place.