I travel a fair bit for work - crowded airport lounges, windowless hotel conference rooms, overpriced restaurants and the occasional glimpse of something interesting through a sticky taxi window. It's not as glamorous as you might imagine.
But every now and then, you get sent somewhere that makes you want to get out and explore. Chicago is one of those places.
One of the first things that struck me about the city was the architecture. It's an extraordinary collection of buildings. Old skyscrapers sitting alongside modern glass towers, the bridges spanning the famous river and an entire skyline that is determined to show off. One of the most recommended things to do in Chicago is the architecture boat tour, and I can add my voice to that chorus!
Chicago has quite a history, much of it shaped by the river itself. The tour gave me an entirely new perspective on the city. Looking up at these unique buildings from the water, learning the stories behind them, you begin to appreciate just how much personality Chicago has.
While on tour, our guide shared the story of the Chicago Fire and Mrs O'Leary's unfortunate cow. As he was telling the tale, a long dormant memory was activated in my brain. I could suddenly see a bird's-eye view of the shape of the city in my head. I had memories of creating firebreaks, bulldozing the industrial heart of the city to save it... I'd been here in 1871!
Well, actually, I'd been here playing SimCity in the early 90s. But that story of the Chicago Fire triggered a memory of playing that game's scenario again and again. Suddenly I recognised the layout of the city and knew exactly where we were in relation to parks and bridges and other landmark sprites.
There was another topic that also featured heavily in my childhood. You can't have grown up a Gen-X kid without acknowledging Chicago's sporting heritage... and while I don't know baseball, I do know the Chicago Cubs and their 108-year wait between winning the World Series. It was a pop-culture reference that I understood.
Of course, they broke that streak with a win in 2016 (yes, that really was TEN YEARS AGO). I did make my way down to Wrigley Field. Enjoyed a proper Chicago hot dog (they have pickle dispensers)! And had a giggle at how many baseball rules appear to be made up... not all outfields are the same size, and if the ball goes into the ivy hanging over the back wall at Wrigley Field then you don't get a home run 😂
One of the unexpected highlights of the trip was Northerly Island.
For most visitors, it's a stretch of wild parkland beside Lake Michigan, offering spectacular views of the Chicago skyline. For me, it was something else entirely... I learnt to fly here.
It used to be Meigs Field, and if you've ever spent any time playing the older versions of Microsoft Flight Simulator, that name might ring a bell. Meigs Field was the default starting airport in early versions of the game. For years, countless virtual pilots began their adventures sitting on that little runway beside the lake.
I'd spent hours flying around that part of Chicago on a computer, long before I ever imagined I'd visit the city. And now I found myself standing on that very spot.
The airport itself is long gone. Like the rest of the city, there's a good story to go with how the city shut down the airport (bulldozers tearing up the runway overnight). But the location is still there, and so are those skyline views.
It was a strange little moment of nostalgia. A place I'd known for decades without ever having actually visited.
Funny how video games can do that.
I'd never visited Chicago before. But between fighting the Great Fire, following the Cubs and learning to fly out of Meigs Field, it turns out I'd been exploring the place for most of my life.
Chicago was brilliant. It felt like coming back to somewhere I'd never actually been.
