Before visiting Chicago, I expected it to feel a bit like New York. In some ways, it does. The skyline is incredible, the architecture is on another level and there's that unmistakable buzz you get from a big American city. But Chicago somehow feels easier. It's cleaner, more relaxed and far less hectic, and I never felt as though we were constantly rushing from one thing to the next.
One of the first things that struck me was the architecture. It's one of those cities where you find yourself looking up constantly, with historic Art Deco buildings sitting alongside huge glass skyscrapers and the river running straight through the middle of it all.
If there's one thing I'd tell anyone to book before they go, it's the architecture river cruise. I'll admit that I wondered whether it could really be as good as everyone said, particularly as spending 90 minutes listening to somebody talk about buildings didn't immediately sound like the highlight of a city break.
It was brilliant.
Seeing Chicago from the water gives you a completely different perspective, and understanding the stories behind the buildings made me appreciate the city so much more. By the end of it, I was pointing out architectural details as though I'd developed a lifelong interest overnight.
Another highlight was our afternoon at Wrigley Field, home of the Chicago Cubs. I knew very little about baseball before we arrived, but you don't really need to. The whole experience is as much about the history and atmosphere as it is about what's happening on the pitch.
Wrigley Field opened in 1914 and there are still little traditions that make it feel wonderfully old-school. There's a live organist playing during the game, the famous scoreboard is still operated by hand and the ivy-covered outfield walls are instantly recognisable even if, like me, you aren't particularly knowledgeable about baseball.
We watched the game from a private suite and completely bought into the whole experience, although I probably spent almost as much time investigating the dessert trolley as I did trying to understand the rules. I still couldn't confidently explain everything that was happening on the pitch, but by the time we left I completely understood why people love going.
Chicago is also a very good city if you travel largely through your stomach, which we tend to do. Obviously we had to try the deep-dish pizza. It was enormous, one slice was plenty and I'm glad I tried it, although I'm not entirely convinced I'd swap a normal pizza for one every week.
We also learnt that Chicago takes its hot dogs extremely seriously. There's a whole system to a classic Chicago dog: mustard, relish, onion, tomato, pickle, peppers and celery salt, and absolutely no ketchup. Apparently asking for it is close to a criminal offence, so consider yourselves warned.
What I liked most about Chicago, though, was how easy it was to spend time there. We could sightsee in the morning, stop for a long lunch beside the river and then wander without feeling that we needed to race across the city ticking off another five attractions. There are world-class restaurants, brilliant museums and some of the best architecture I've seen in an American city, but it never felt overwhelming.
It's also somewhere I'd use as part of a bigger North American journey. A few nights in Chicago before heading into the Canadian Rockies, across to Vancouver or onwards to Alaska would give you a completely different start to the trip, and I'd much rather build an itinerary around contrasts like that than simply string together several similar cities.
Chicago wasn't somewhere I'd spent years dreaming about visiting, and perhaps that's partly why I enjoyed it so much. I went without a huge list of expectations and discovered a city I'd happily return to.
A place that stayed with me
Wrigley Field. Not because I've suddenly become a huge baseball fan, but because it felt so completely different from the modern sporting venues I'd expected. Sitting there with the organ playing, looking across the ivy-covered walls and watching someone manually change the scoreboard felt like experiencing a little piece of American history rather than simply going to a game.
A moment I'll never forget
Really seeing the skyline from the river for the first time. I'd seen countless photographs of Chicago before we went, but being down on the water with those buildings towering above us was the moment I realised I'd completely underestimated the city.
One thing I brought home
Don't overlook somewhere simply because it isn't the obvious choice. Chicago wasn't at the top of my USA wish list before I went. It became one of my favourite North American cities once I did.



