When small talk gives way to deeper conversations, a world of thoughtful insight reveals itself. Penetrating through questions about where one works and lives, opportunities to know someone more deeply start with simple, but profound questions.  

“What travel destination changed the course of your life?”  

Nine little words strung together with a real chance to know someone. At the best dinner parties or conversations over drinks at a bar, questions such as this have been served. It is one of my favorite questions to answer and it is something I am always happy to investigate in a new way.  

As a kid growing up in rural Oklahoma, I often dreamed of a life in a larger city. I would daydream and create a world vastly different from my own. Those fantasies shared some common themes. I always pictured a fantastically decorated apartment in a walkable neighborhood. I dreamed about walking to work each morning, catching a train downtown, and working in an office tower at a job I really loved. Every night, I would return home to my neighborhood filled with local restaurants, bars, and shops. In my 12-year-old mind, this felt like the perfect scenario.  

I did not know it at the time, but I was dreaming of Chicago. On three separate occasions, I have visited the Windy City. Each visit to Chicago has been transformational. My last trip was defined by experiences I will never forget.

For a time, a fraternity brother of mine lived on the north side of Chicago. On this visit, he was generous enough to let me borrow his apartment for a few days while he stayed with his partner. On the train, walking “home,” exploring downtown, and bouncing from local shops to nearby restaurants, I got a small taste of what it would be like to live in this city. For hours, I walked. I walked deep into the night, overjoyed with the experience of being somewhere new.  

As I explored, I arrived at an opinion that left me jealous. I dearly love Seattle and the Pacific Northwest. I also love lots of other cities I have visited and called home. But, without hesitation, I believe downtown Chicago to be the most beautiful in the United States. Walking through the concrete canyon and venturing through Millennium Park, the architecture of the city struck me. With a camera by my side, I found myself in awe. I attempted to capture the city through my lens in every conceivable way. I fear I still did not do this wonderful city justice.  

I also found the city to be highly walkable and public transportation reliable. Without a car, I relied on my feet and the train to get me where I needed to go. During the trip, I never struggled to reach any destination on my wish list. This felt like a continuation of that dream I used to have. This time, I once again found myself jealous and longing for a Seattle that felt the same way.  

My fraternity brother and I are both gay. “When in Rome, do as the Romans do.” In Chicago, this meant we spent a lot of time in Boystown. I quickly learned the hard way that Chicago bars do not close until four in the morning. I will not share my exploits here (this is the internet) but ask me to join you for a drink sometime. I promise, I have some funny stories to share.  

As I left Chicago, it snowed. It was late April, and the heavens were dusting the Midwest with powdery snow. My first two trips to Chicago were both in February. Leaving our hotel, I stepped outside into a world where the windchill dropped below zero degrees. As I watched the snowfall from the back of a taxi, it reminded me of why I will never call this city home. I really hate the winter.  

Be good to each other,  

Nathan