Via Chicago: My Christmas Journey from Kitchener to the Windy City
This December, I got the itch to experience the holidays somewhere different—somewhere with magic in the air, twinkling lights, and a pulse that makes you feel alive. This year, I decided to trade in Kitchener’s cozy charm for the bold, festive spirit of Chicago. I flew Porter Airlines out of Billy Bishop Toronto City Airport and spent a few days immersed in deep-dish vibes, twinkling skylines, and that unmistakable Midwest warmth.
And yeah, I had Wilco’s Via Chicago in my head the whole time.
Getting to Billy Bishop is a breeze compared to Pearson, and that’s part of the charm. Flying Porter is like stepping back in time, in the best way possible—complimentary drinks, cozy seats, and a quick hop across the lake that drops you right into the heart of Chicago. By the time I landed, the city's skyline was lit up like a snow globe, welcoming me with open arms and festive cheer.
As soon as I dropped my bags, I headed straight to Millennium Park. Seeing The Bean—or Cloud Gate if we’re being proper—in the winter is a whole different experience. Snowflakes danced in the reflections, and everyone had that holiday sparkle in their eyes. The ice rink beside it was packed, the music was festive, and the mood? Pure joy.
I couldn’t be in Chicago and not make a pilgrimage to Wrigley Field. Even in winter, there’s something sacred about that place. Just walking around the outside, I could feel the history humming. A few blocks away, I grabbed a bag of the iconic caramel mix from Nuts on Clark. It warmed my hands and reminded me why Chicago snacks hit different.
I treated Heather and I to a classic steak dinner at Gibsons. Thick cuts, rich wine, and holiday lights glowing through the windows—it was exactly what I needed. We slid into a booth once occupied by Saturday Night Live stars at the Billy Goat Tavern, had a cheezborger (yes, cheezborger), and soaked in the old-school atmosphere that feels like a Chicago rite of passage.
One of the highlights of the trip? An architecture boat tour at night. Gliding down the Chicago River, wrapped in a blanket, hot chocolate in hand, and gazing up at the city’s towering skyline—man, it was cinematic. Buildings like the Wrigley Building and Marina City lit up the river like a Broadway show. Chicago knows how to do drama, especially at Christmas.
The Christmas trees scattered around the city were little explosions of joy—each one with its own personality. The tree in Millennium Park was massive and glowing, and even Trump Tower, with all its controversial grandeur, was impressive reflecting the festive lights of the city.
Throughout the trip, I kept coming back to Wilco’s haunting track, Via Chicago. It felt like the perfect soundtrack—melancholic but hopeful, twisted and beautiful. The line "I dreamed about killing you again last night and it felt alright to me…” floated in my ears as I walked the city streets, thinking about life, love, and how sometimes a song can make a city feel like home.
I flew back to Canada full—full of food, memories, and a whole lot of holiday magic. Chicago at Christmas has a rhythm all its own, and I was glad to follow the beat. I didn’t just travel to Chicago—I went via it, through it, and maybe even left a little piece of myself behind.
