before I start with my thoughts about your essay I want to tell you that I was in Chicago two times, in 1987 (when Sears Tower was the tallest building of the world) and in 1997 (the "bean" wasn't yet installed!) - both times in summer. Ahhh, memories...
It makes me happy to see your essay covering a whole visit to this amazing city, and above all you started with food! Tasteful! Your street shots are impressing, a wonderful variety of different situations well seen and recorded. I'm not familiar with Adobe Spark but it is fun to scroll with you through Chicago. Thanks for taking us with you.
Finally I'm nitpicking: I'd loved your essay even more if you stayed either colour or bw for one complete theme. F.e. color for food, architecture and pictures of Jen, b&w for street shots and pictures at the Bean. But that is only my personal taste.
I'm already looking forward to your next visit to a foreign place!