Chicago (and Traveling Alone)

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Last week I took a little solo trip to Chicago, mainly for Market Days but also to check out a new city. Chicago has always been on my short list of cities to visit, and I felt that it was a good time in the year (and in my life) to finally take the plunge. This was also my first solo trip and I may already be addicted!

Chicago Skyline

I must say, following this trip, Chicago is a great city. I’m glad I made it my first stop in my traveling solo series (if there ever will be such a series)! And at this time of year the weather was absolutely amazing. The four days I was there it never got past 85 degrees and the humidity was practically zero.

Chicago L

I’ve always been more of an urban guy, so while some people might balk at the fact that I took a vacation to Chicago, I absolutely loved it. To me, Chicago wasn’t as crazy as New York, and the city just felt cleaner and more sophisticated. I also loved their public transit system. I was able to get everywhere I needed to go and only had to Uber once (and even that wasn’t totally necessary)!

Calder Flamingo

The arts are HUGE in Chicago. I could feel it as soon as I stepped off the plane, right there in the airport. Everywhere you turn there’s music, sculptures, paintings, even the buildings. For someone like me, it was almost paradise. I got to check out quite a bit of the urban art and the Art Institute as well. The latter is a gigantic museum, and I would have needed a whole weekend just to go through it in its entirety! But spending a few hours (like I did) was better than nothing.

"Ohhh... Alright..." by Lichtenstein

I had no idea so many famous works of art resided in the Art Institute! I couldn’t stop taking photos, but I kind of had to because the battery in my phone is absolutely terrible.

"The Basket of Apples" by Paul Cézanne

I also checked out The Field Museum, which was just okay. I much preferred the Art Institute, but maybe I’m biased. I think the Natural History Museum here in Washington is one of the best. I didn’t get to take an architecture cruise, but that’s on the top of my list for my next visit there.

Feet on the Skydeck

Traveling alone was a really interesting and eye-opening experience. In the weeks leading up to the trip I was so nervous at the thought. Every day I would Google things such as “how to travel alone” or “is traveling alone safe” and read everything that I found. While I was nervous, I really wanted to take this step as kind of a confidence booster and really do something totally on my own, with no help from anyone. I think it has definitely boosted my confidence and unearthed some skills and traits I never thought I had. It was also really liberating. I was completely on my own and didn’t have to worry about compromises. Plus, waiting for a table at restaurants was nonexistent since it’s easy for them to seat a solo diner!

Overall, it was a really great trip, and I’m already thinking about where to go next! As long as my bank account continues to cooperate…