We were not planning a family trip to Chicago this year. But given the insane fuel costs due to the war in Iran on top of the fact that we’re current in the U.S. Open season, flying directly back from SFO to JFK this week would have been ridiculously expensive. In the end, we decided to fly to Chicago, stay three nights here, then fly back to New York on Friday; we also used miles to book these flights. This wasn’t the worst idea in the world: both Chris and I love Chicago; we’ve both come to visit separately for both work and pleasure. Kaia has never been, and so we thought it would be fun to spend a few days here together. Plus, our timing is right: not only did the Obama Presidential Center just open, but the world’s FIRST Hello Kitty Cafe also just opened here!
Since it’s still a working week for me, I had to spend several hours this morning working and doing meetings before going out for the day. Chris took Kaia out (and to the Hello Kitty Cafe already!) in the morning, and I ended up meeting them at Millennium Park, right where the Bean, aka Cloud Gate, is. As I walked down from our hotel to meet them, I started thinking about all the times I’d previously come here and what I did each trip. I’ve done about half a dozen work trips here over the years, and I have always tried my best to eat at interesting restaurants or grab coffee from fun cafes to maximize my time here. On one work trip I took here back in 2010, I remember I had to arrive by Sunday for an early Monday morning meeting. So I took advantage of the day and arrived early Sunday to spend the whole day exploring Chicago by foot, which included a few hours at the Shedd Aquarium (AMAZING place!).
The one non-work trip I did was for a girls’ Thanksgiving long weekend trip in 2009. That was the trip when I stumbled upon a German-style Christmas market just a few blocks from my hotel, and before my friends arrived from San Francisco. There, I had some good chatter with the German vendors there, who happily educated me about the glorious and magical Christmas markets I could experience if I traveled to Germany during the holidays. I had no idea that was even a thing back then, so my curiosity was piqued. It was then that I decided that I absolutely had to go to Germany during the holiday season. Four years later, Chris made that dream a reality for me, as we took our first trip to Germany (Berlin and Hamburg) during Thanksgiving week 2013! That trip cast a spell on me for European Christmas markets. After that trip, we just kept on going with the European Christmas market Thanksgiving week trips. Fast forward to 2022 and to present, Kaia has now also joined us for four of these trips! A new family tradition was born, all ignited from my very first leisure trip to Chicago in November 2009.
I love Chicago for many reasons. I love the layout of the city, the river, the lake, and the L. I love how walkable it is. I love the parks and the green spaces. I love the food scene here. I especially love the great things I’ve discovered here, including the beginning of my obsession with European Christmas markets and all things related to them. So I’m quite happy to be back.