In early August I took some vacation time to celebrate the end of summer classes and to refresh before my final semester of grad school and a busy fall season at work. I wanted a bit of adventure and felt antsy to get out of Buffalo for a few days, so I booked a ticket to Chicago, because it felt like the obvious choice. 

I’ve been going to Chicago since I was a little kid, mostly to visit my mom’s family, who live outside of Wheaton. It was my first big city, and always felt extravagant in the way I longed for life to be. It’s where I got dressed up for afternoon tea at the American Girl Place on Michigan Avenue, with thick snow falling on the fancy coat Mama bought me. It’s also where I saw my first Broadway show (Wicked) and where I took my first shot (a pickleback in a corner pub). I remember that first stop at Navy Pier where I tried Dippin’ Dots for the first time. And there was the formative weeklong conference in high school at Northwestern where I explored a career in medicine. My childhood and adolescence are punctuated with memories of the city, and I feel a love and connection to that place that keeps pulling me back. 

In August I had another round of “firsts” in Chicago, including my first meal at a Michelin star restaurant, an evening architecture tour by boat, and drinks with my dear friend Katy and her husband at Cindy’s rooftop. The trip was significant for me because I took it alone—not that I haven’t traveled by myself before, but this was the first vacation I’ve taken that didn’t hinge on the presence of another. It felt good to take up space and to follow my own whims and curiosities. 

I walked miles and miles of the city while nibbling on a peach and ginger scone, and stood with my neck craned back to follow the corkscrews and freefalls of airplanes performing in the Air and Water show. I ate two oversized cornettos on the roof of the Starbucks Reserve Roastery and an entire plate of churros at a Mexican bar by the river. I sipped black tea on a bench outside of the Museum of Natural History looking out over Lake Michigan on a Tuesday morning. The blue water was impossibly bright, and while I watched the sparkling waves I pondered my life so far, which has been lived between two Great Lakes. I took an Uber Black back to my hotel just because I could.

On Sunday afternoon I stumbled on my brother’s old apartment, quickly recognizing the McDonald’s where we got breakfast on Sunday before church. My brother worked as a junior analyst at a global investment bank in Chicago during my last two years at Calvin, which provided an excuse to take the short train ride from Grand Rapids into the Ogilvie Transportation Center downtown, which was just across the river from his office building. My favorite of those memories is the trip shortly after my twenty-first birthday where I asked Nathan to teach me how to navigate the foreign world of bars (and alcohol). 

He took me to a speakeasy where I discovered the magic of Baileys with coffee, and after several stops to meet up with his friends, we ended the night with my first shot (see above) and pints of ice cream from CVS. In the morning we went to Do-Rite donuts for fried chicken sandwiches served between two halves of a donut. It was perfect, and I felt so loved to have a brother who takes me on adventures and makes my world bigger and more spectacular. 

And maybe that’s what I love about Chicago—it always makes the world feel a bit bigger, a bit more spectacular, and it always leaves me wanting another weekend adventure. So Chicago, I’ll be back—please have hot dogs and cold, clear days ready for me. 


  1. Tavia

    Lots of good memories in this essay!

  2. Louise Kelly

    What good memories you have of Chicago

  3. Katy

    All the fun city things! It was one of my favorite summer weekends! 🙂


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