Experiencing and Growing in Chicago: A Father-Son Journey Through Culture, Curiosity, and Leadership

Downtown Chicago

“Dad, why are the buildings so tall?”

That was one of the first questions my five-year-old son asked after we arrived in Chicago this past spring. It was his first time in the city. It wasn’t mine.

In fact, Chicago was the first American metropolis I ever visited. I was 16, spending three weeks with my pen pal Chris in Michigan in the summer of 1999. I was instantly fascinated. In some ways, I fell in love with the skyline, the energy, the unfamiliar rhythm of it all. I’ve returned many times since, both for work and for personal reasons.

Willis Tower (formerly known as Sears Towers) in between buildings and the Chicago Skyline from the south of Grant Park

So when I started thinking about a city I'd want to share with my son, Chicago felt like the obvious choice.

Maybe he’d see what I saw back then. Maybe I could awaken in him a curiosity about the wider world. Maybe he’d start to understand how much we grow when we travel with open eyes and open hearts.

🏨 The Planning: Pools, Priorities, and Purpose

We planned the trip together. His number one requirement? A hotel with a pool.

He had set a goal for the summer: to become a strong swimmer. He wanted to be ready for lakes, rivers, oceans—wherever adventure might find us.

So we compromised:✅ Big city discoveries for me✅ Plenty of swimming time for him

In our seven days in Chicago, we went to the pool 14 times. The confidence he gained in the water was real. He was proud. And so was I. But that was only one of the many things we’d take home from this journey.

Our pool at the Homewood Suites

✈️ Getting There: Planes, Perspective, and Austrian Hospitality

We took off on April 3rd with Austrian Airlines, flying directly to Chicago on the brand-new Boeing 787 Dreamliner. I love flying, especially with a curious five-year-old, and the journey itself became part of the experience. This aircraft was worth exploring: new seating, more comfort, and as always, impeccable Austrian catering. Sometimes, consistency matters. Good service, good food, a little piece of home, even at 35,000 feet. As I sipped an Eiskaffee midair, I realized: even in the clouds, we’re learning about culture.

Austrian Airlines serves a really nice variety of typical Austrian coffee

🏙 Discovering a City—Through a Child’s Eyes

The view from our hotel room was stunning for me. For him, it was mind-blowing.

The view from our hotel room on the 19th floor

“Why are there so many tall buildings?” “What are they all for?” “Can we go up to the top?”

Of course we could. We visited both the Willis Tower (formerly Sears Tower) and 875 N. Michigan Ave (the John Hancock Center). From up high, the city becomes a map. It makes sense.

The view from the 103rd floor of the Willis Tower

And that’s when it hit me again: Perspective changes everything.

Just like in leadership. When things feel overwhelming, taking a step back, or looking from above, can bring clarity. This is a mindset I’ve always valued, and now I could see it awakening in him.

🐧 Penguins, Polar Bears & Learning to Pivot

One of our stops was Lincoln Park Zoo. We went with a mission: to see penguins.

Spoiler: they weren’t particularly cooperative.

But instead, we discovered so much more: A lion sunbathing in the spring chill. A surprisingly social polar bear. A winding walk through ecosystems we hadn’t expected.

We came for one thing. We left with something different, and maybe more valuable.

At the Lincoln Park Zoo

Leadership lesson?🎯 Focus is great. But flexibility is essential.

🚇 Walking the City: Steps, Snacks, and Street-Level Stories

I love navigating cities on foot and by public transport. You see more. You feel more. And you witness the everyday life of people who call the place home.

CTA took us everywhere we wanted

We took buses, trains, and lots of long walks. With a five-year-old, that means a bit of planning, snacks help, frequent breaks help, curiosity helps even more.

And honestly? He loved it. Chicago unfolded not as a checklist of tourist stops, but as a stream of stories we created together, one intersection at a time.

Sightseeing in Chicago – Cloud Gate, also known as 'The Bean

🇸🇪 Tracing Roots in Andersonville

As a Swede living abroad, I’m always drawn to places with traces of home.Chicago’s Andersonville neighborhood has deep Swedish roots: flags, bakeries, names, and old stories.

“Dad, are there Swedes here?” “Can I talk to them in Swedish?” “Do you forget your language when you move away?”

We ended up talking about emigration, about the Swedes who came to America in search of something better, about the lives they left behind and how they shaped the place they arrived in.

"Will I still speak Swedish and German if I live somewhere else when I grow up?"

Questions like these are windows into deeper truths. About belonging, identity, and history. And they’re essential if we want to raise global citizens who are both grounded and open.

🏀 Loyalty and Letting the Game Play Out

Near the end of our stay, I took my son to a Chicago Bulls game.

It was everything I hoped it would be: high energy, lights, popcorn, big emotions.

Chicago Bulls vs. Miami Heat at the United Center

He jumped right in:

“Let’s go Bulls!” and “Defense!”

But when the Bulls started losing in the second quarter, he leaned over and asked:

“Can we go home now?”

And that gave us a chance to talk about something important:

You don’t leave when your team is down. You stay. You show up. In sports. In life. In leadership.

We stayed. The Bulls came back. Final score: 119–111.

🌍 Final Thoughts: One City, Many Lessons

After a week in Chicago, we flew home to Austria: a proud child, a reflective father, and a shared experience neither of us will forget.

He called me “Dad” for weeks after the trip. I smiled every time.

A seed has been planted. Curiosity, resilience, wonder. And perhaps, in his own way, a little citizen of the world is beginning to grow.