Back in 2025, after returning home from another “status run” trip — one of those whirlwind airline journeys designed to earn frequent flyer miles and elite status — my 14-year-old son Gregory said something that stopped me in my tracks.
He told me he thought it was cool that I travel around the country so often. But then he added something else. Gregory said he sometimes felt a little slighted. From his perspective, I was always flying to interesting places and seeing amazing cities, yet he felt like he rarely got the chance to experience those places with me.
At first, I thought the statement was a little preposterous. For as long as I can remember, Gregory and I have flown down to Memphis to visit my parents, and we’ve taken plenty of road trips together to Michigan, Indiana and other parts of Illinois. In my mind, those trips counted as meaningful travel experiences.
But Gregory followed up with a comment that made me pause.
He said he had never been to New York City. He had never been to Seattle.
And suddenly, I realized he was right.
Why Traveling With Your Kids Matters
While I had been fortunate enough to visit cities across the country through my own travels, my son — the person I care about most — hadn’t had the same opportunity to experience many of those places himself. That realization stuck with me and eventually inspired me to write this story.
Growing up, flying around the country simply wasn’t something my parents did. Travel, at least the kind that involves airports and boarding passes, wasn’t a regular part of our family life. In fact, if I’m being honest, I’ve probably put my parents on more flights in the past few years than they’ve ever booked themselves.
My love for travel developed later in life. It came from curiosity — the desire not just to read about different places but to experience them firsthand. You can learn a lot about a city by reading articles or watching videos, but there’s something completely different about walking the streets yourself, meeting people and feeling the unique rhythm of a place.
Gregory’s comment made me realize that while I had been enjoying those experiences, I hadn’t always made it a priority to share them with him.
If you spend any time scrolling through social media, you’ll see parents traveling all over the world. Some take solo trips, while others go on romantic getaways or what people jokingly call “baecations.” There’s nothing wrong with that — everyone deserves time to recharge. But Gregory’s comment made me reflect on how often parents include their children in those adventures.
Travel can be expensive, and adding another plane ticket or hotel room can quickly increase the cost of a trip. Still, experiences are something children carry with them for the rest of their lives. In a world where many kids spend hours looking down at screens — phones, tablets, and video games — travel encourages them to look up and engage with the world around them.
It shows them that there is far more to discover beyond the walls of their home or the boundaries of their neighborhood.
After that conversation, I made a promise to Gregory that we would begin exploring more together. And that exploration didn’t necessarily have to start with a plane ticket.
We live in the Chicagoland area, which means one of the greatest cities in the world sits right in our backyard. Chicago offers world-class museums, incredible architecture, diverse neighborhoods, and some of the best food in the country. Yet like many locals, it’s easy to take those opportunities for granted.
So Gregory and I made a commitment to experience Chicago more intentionally. That includes visiting museums we’ve talked about but never explored, taking occasional overnight stays downtown in The Loop and simply walking the city to discover what makes each neighborhood unique.
Recently, Gregory has also developed an interest in baseball, which has created another opportunity for us to travel together. This year we plan to watch the Seattle Mariners play twice — both at home in Seattle and on the road in Detroit and Cleveland. We also hope to catch games in New York City, Milwaukee, St. Louis, and San Diego.
Of course, living near Chicago means we’ll attend several White Sox games as well. And while it pains me to say it as a lifelong South Side fan, we may even make a visit to the North Side to watch the Cubs play.
These trips aren’t just about baseball. They’re about the moments in between — the conversations in airport terminals, the excitement of arriving in a new city, and the late-night meals after a long day of exploring.
Those are the moments that turn into lasting memories.
Gregory’s comment that day reminded me of something simple but important: if we’re fortunate enough to travel, we should share those experiences with the people who matter most.
Whether it’s flying across the country to Seattle, spending a weekend in New York, or simply exploring Chicago together, those experiences allow children to see and understand the world in ways they never could from behind a screen.
Because in the end, travel isn’t just about the places you visit.
It’s about who you bring along for the journey.
Let's Take a Day Trip 
Leave a comment