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A Week in the Windy City

Chicago is one of my favorite places in the world. When Sam and I were looking at options to take advantage of the work-from-anywhere situation, that was on the top of the list. I’ve wanted to show him the city for a while, and so we booked a week here to work from our company’s Chicago office and spend some time exploring!

Anyone who knows me knows that I am weird about food, but Chicago is one of the few places where I actually plan out the bulk of the meals in advance instead of just wandering and finding restaurants. Obviously anyone visiting has to try Chicago-style pizza, so that’s Giordano’s or Lou Malnati’s or Gino’s. Personally, deep dish isn’t my favorite style of pizza, but I also happen to think that all of those places do incredible regular crust pizza as well. Then there’s Portillo’s, for hot dogs and Italian beef and, most importantly, their chocolate cake milkshake. Eataly does great food and is also fun to shop for groceries in. There are so many good restaurants and caf├ęs and brunch places. This time, I met up with a friend at a place that had to-die-for gnocchi and a gelato flight, which was probably my top meal of the trip!

Chicago has stellar museums. I would always recommend the Field Museum and Shedd Aquarium, but the one that I made sure Sam saw was the Art Institute. Fun fact, it has the largest collection of impressionist art outside of the Louvre! It also has American Gothic, and Nighthawks, and a collection of miniatures, and beautiful stained glass. We got lucky this time and the Obama portraits were on tour there, so we got to see those up close.

Sam was shocked to find that The Bean is in fact, a large metal bean shaped sculpture! Millennium Park is always fun to wander through. I have two other recommendations I always make for first time visitors. The first is an architectural river tour. It’s a great way to see the city, and Chicago is a city known for the architecture! I’ve done the boat tours twice and learned a lot. Never call it the Willis Tower, though. It’s the Sears Tower. Always. The second recommendation I have is to go see Second City. They’re a great improv group, and a lot of SNL alumni started there. When I go, I always hope one of them will make it really famous and I’ll have gotten to see them early in their career. When Sam and I went, it was the first live show I’d been to since the beginning of COVID, and it was magical.

Depending on the season, try to go see a game at Wrigley! The tickets are a little more expensive now that they’ve broken the curse, but the stadium is super cool and historic. I’ve sat everywhere from the upper nosebleeds to right behind home plate, and it’s always been a fun afternoon experience.

We were there over the 4th of July, and got to walk along Lake Michigan as the fireworks went off. It was such a good week, and I’m already trying to figure out when I can go back!

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