Spring 2022: Chicago

I always wanted to visit the Windy City but somehow, this became the last major US city I got around to touring. Over the years I would look at airfare and it always seemed to be in the dead of winter which, for me, is not exactly the ideal time to head north. I would occasionally have a layover at O’Hare, see the skyline, and think I have got to visit this place!

Finally, to use up an airline credit, I scored a $99 round-trip ticket so Chicago was finally going to happen. I did take advantage of my remote status and worked a few days during the week but I still had plenty of time to explore the city.
And what a city! The architecture was amazing. The city teemed with life. And I don’t think I will ever forget the amazingly loud screeching sound of the L trains overhead. I tried to pack a lot into a week but I was pretty happy with what I did.

The first day was a bunch of travel. The flight into Chicago was an early one and it was well past check-in time at the AC Hotel before I got my room. I ended up working from the lobby which wasn’t the most comfortable. I did jump right into the Chicago experience and had a deep-dish pizza lunch at Giordano’s. I’m not going to lie, it wasn’t my favorite pie but I’m glad I tried it.

The next day it was time to venture out a little farther. I had Portillo’s for lunch and I get how the Italian Beef can be addicting. I then walked to Navy Pier and took in the skyline and the lake views. For early April, I had amazing weather over the first few days so I took full advantage! People recommended the architecture boat tour and while I am not a huge tour fan, I decided to take one with Shoreline Sightseeing and I am really glad I did. The cruise down the river and seeing and hearing about all the buildings was worth it. Dinner was a treat at Au Cheval and I got extremely lucky snagging a bar stool at this small but popular place. I had a crazy good burger. Crazy good.

The next day I balanced online work with some food stops including Do-Rite Donuts and Chicken for breakfast, and a quick jaunt across from the hotel to Side Door. I wasn’t super hungry for dinner so I had something light at Monk’s Pub and then it was time to see Aladdin at the Cadillac Palace Theatre! The show was pure Disney camp but it was still live theatre which is always enjoyable. After the show, I made a pitstop at the Shake Shack to finally try it out. The verdict: not too shabby. I wouldn’t hurt someone for the food, but it was pretty decent.

Saturday was a big wandering around the outskirts of Chicago day. I took full advantage of my Venta pass and even took the bus. I walked around the old town and down north ave until I hit Lincoln Park. I went all the way south to Hyde Park and had a delicious salad at The Promontory. I went back up towards the city and walked around Chinatown. The back up north some more until I hit the neighborhood with Big Star taco.

Saturday was a big day so on Sunday, I largely chilled. I did make time for a stop at the Museum of Contemporary Art and spent some time walking around. I had a late lunch at Grand Lux. I napped. I watched TV. I walked around a bit and I completely forgot I had about a ticket to The Second City. I awoke early on Monday thinking ‘I need to laugh’ and immediately remembered I kept feeling like Sunday was a little TOO lazy. I was a bit bummed about that, but now I have another item to do on my next visit to Chicago.

The last night in town, I decided to splurge on a good meal, and Chicago is known for steakhouses. I decided on Kinzie Chophouse and I had a seriously fun and amazing meal. I enjoy sitting at the bar, especially when dining alone. The bartender was an absolute joy to chat with and the food was spot on delicious. The wine flowed nicely and it was just a perfect way to wrap up my Chicago experience.

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