I spent a weekend in Chicago with Kate (my wife). Not for any particular reason other than to mix things up a bit. We’ve spent a lot of time traveling to small places, and natural places over the years, and we decided that we really wanted a night on the town. So, we booked some flights, send the kids to Grandma’s, and off we went!

Kate used to go to school in Chicago, so she had some stomping grounds, and fond memories of the place, and I was delighted to get an opportunity to get to be a part of reminiscing with her, letting her guide me and show me a city she loves so much.

Our primary goal was to go to a concert for AURORA, one of Kate’s favorite artists in the last few years. We got VIP seats, which honestly might have ruined concerts for me forever. The venue was The Aragon, and it was great. The acoustics, our seat, the lighting, all of it. Definitely was different than my typical concert experience being on the floor, but I liked it a lot.

It was bitter cold in the city, with wind that cut like a knife, and yet the city seems so good at adapting to the cold. Every coffee I ordered was way hotter than I’m used to, but once I went outside with my cup it made sense. The extra hot coffee warmed our hands nicely, and cooled to a warm temp quickly. My coffee was done in just a few short blocks, warmed my soul, and made the rest of the walk much more comfortable, just in-time for the next coffee shop, hotel, L station stop, store, or whatever was next.

Not to mention, everyone just looks so well dressed. I couldn’t get over just how good everyone looked. With all the cold comes extra layers, and extra opportunities to dress up in practical clothing that also warms at the same time. I have been lamenting recently about how I “wish hats were cool again”, and wouldn’t you know it – I just haven’t been in the right places because people wore cool hats, and looked great in Chicago. Colored hair, beanies, fedoras, newspaper boy hats…all of it. You just don’t see people dressed like this in my small town. If you do, you really stick out. Kinda makes me sad, really. I wanna dress that nice and not feel like I’m in a costume.

Combined together, you found that the fact that your face was numb (as I write this my cheeks still feel wind chapped!) to not be that big of a deal. It just made the coffee that much more pleasant. The rides on the L that much better, and the serendipitous moments where you found something cool when in the moment you were just trying to find a warm place to get your bearings for a moment.

I really loved traveling on the L. It is always fun to utilize public transportation, because it turns simple errands into a journey when you’re new to the area. A little puzzle to solve, while also practically solving your problem and saving you some money in the process. The L is particularly great because some of the lines in the loop are elevated and double as an amazing way to tour Chicago. Really gives you a chance to get up close to different buildings, and see some of the city all for a $15 weekend pass.

In many ways, it felt to me like I was in a time machine. The city has its own culture, and you can feel it. It feels old and new, cool, and classic. I see influence from its architecture in such a quiet way that I never appreciated before. As someone who spent a lot of time traveling and around places pertinent to the frontiers, gold rushes, and the westward expansion of the US, It’s one of the rare times I really felt a classic American culture that still felt very much alive and intact. Most history comes in the form of photos, ruins, or plaques. In Chicago, it’s just…there. Intertwined with everything else. It’s really hard to find that in the United States, because we’re just so damn young.

Anyway, it was a great trip. Had a great time, ate great food, drank lots of coffee. Will definitely be returning soon. ‘Till next time, Chicago! In the meantime, it’s time to watch my Christmas movies, many of which feature you <3.