Windy City Adventures (2026)
Hello my blog!
It's been some time since I've finished writing something, at least conclusively enough to post it. In fact, it's taken me so long that I'm now writing about a trip I took at the beginning of the year. It's been long enough that I considered just giving up on this blog post, but as someone who doesn't use social media, I've decided to push through. Memories are too ephemeral and I want a means of recording my life. I want to look back and see pictures of my life and the wonderful people in it. And I refuse to use Instagram or any other platform that seeks to use me as a means to make money and continue their evil tech agenda.
Back in March of 2026, I went to visit Chicago with a group of close friends. My friend (and now current roommate — that's a story for another day though!), Sophia, had been attending medical school in the Chicago area for years at that point. With her graduation approaching, we knew we had to mobilize the nerd squad to go and visit her weeks before her move out of Illinois. But hey, at least we made it out there just in time!
The trip was a short one, lasting only four days. And coming from sunny Los Angeles, I had an inkling that we'd experience challenging weather that my weak and spoiled physical composition would struggle with. I say that largely in jest as I've lived through brutal winters in NYC, but Chicago's reputation for wind chill was still looming large in my mind. Despite the bad weather, it was my first time being in the mid-West and I was ready to see and witness what many (Chicagoans) claim to be one of the greatest cities of the United States, while spending time with some of the closest people in my life.
Before going, I did some light research to prepare myself. All I had known prior to this point was that Chicago was known for its brutal biting winds — hence why the city was monikered the "Windy City" — and that it was the third most populous city within the U.S. I did eventually learn that the title of "Windy City" actually didn't refer to the icy lake winds that tormented Chicagoans during the winters, but instead referred to the bluster of Chicago's terrible politicians over the years. But my shallow search for information had still unearthed recommendations for food, places to see, and things we had to try that were quintessentially Chicago.
The first night we trekked out into the cold to make our way to our first Drunk Shakespeare experience. At this point, I had been crowned a Lexapro liege for my anxiety, which meant that any alcohol consumption would have to be light or nearly non-existent. Naively, I assumed this meant that I'd be able to enter the establishment without having my ID with me, which immediately stopped us in our tracks when trying to enter with our tickets. The lady at the front door was kind enough to look the other way once I explained that I was on medication and not planning on ordering alcohol during our time there.
I admittedly was much too sober for Drunk Shakespeare. I was over stimulated by the swinging dildos, raucous shouting, and drunken shenanigans. It's not my thing and I'll definitely pass on the next offer to go, but to quote Honey Boo Boo from my tumblr.edu days, "you have to taste the milk before you buy the cow"! And post drunken Shakespeare, Chicago's iconic Giordano's was in our sights as we had to engorge yourselves upon the city's infamous Deep Dish Pizza.
The deep dish experience was one that I knew I needed to try at least once. And I think I'd like for it to stay an experience I've had exactly once. The deep dish pizza stands as testament to man's hubris. The sheer density due to its many layers of cheese and sauce was sorely underestimated. A single slice was enough to block up the works. An unwise second almost sent me to the hospital pregnant. We ended up leaving the restaurant feeling sick to our stomachs, swearing to never once again eat such an abomination (or at least have fewer slices). Cassie managed to eat FOUR slices that slices. Never underestimate Cassie with anything.
To no one's surprise, our first morning and second day in Chicago began with a rough start. The massive blocks of cheese and sauce had wrecked our digestion and kept us comatose in bed. But a trip to our local coffee shop, some breakfast empanadas, and a croissant had us back on our feet and ready to go.
And we had to be ready to go as we had big plans for the day despite the torrential rains that threatened the whole experience. First stop before our architectural tour of Chicago was at the Purple Pig.
Some white wine was had to start the experience (and I had forgotten to take my medication so we had to make the most of it). Unexpectedly, this place served a grand and delicious meal. We had heard rumors of this restaurant being a great one, but even our expectations were shattered. First course was the mushroom plate. It featured a variety of beautiful mushrooms and was served with a luscious and earthy truffle sauce and some caviar to balance the richness.
The apricot honey spread with toasted bread was a nice complement to the rich course and deeply flavorful dish.
The Spanish-style Octopus, a dish I had chanced upon once in San Diego, was what I was looking forward to the most and absolutely blew my mind away. I've never been a fan of seafood (or octopus to be honest), but this style of preparation has taught me that any dish-regardless of ingredient-can be met to one's tastes.
Some squid ink risotto and Iberian pork helped round out the rest of our meal, and having had our fill, we headed out into the rain to catch our Chicago River Boat Architecture tour.
The Architectural Tour features buildings and designs from across the ages. We learned that a great fire, a tragedy that had burned down most of the city, had provided an opportunity to rebuild the city from almost complete scratch. The Chicago waterfront and city skyline are a testament to man's resilience. That even in the aftermath of the worst moments, people can build back stronger and better.
Chicago is beautiful. I think when people think of the quintessential American city, the Big Apple comes to mind for most folks. However, when thinking of the aesthetics of the ideal American city, Chicago is what most folks believe NYC to be. The city is gorgeous both during the day and the night. It's clean and grand, while still feeling a bit more connected to our collective humanity. It's what people see in their mind's eye when envisioning what a great city of America could look like.
And it wouldn't be a proper evening spend with friends without some drinks and a proper round of gossiping and yapping late into the night.
And of course before we left Chicago, we had to visit the Bean and also stop by the Art Institute.
Emily had never heard of the phrase "flicking the bean", so we took this moment to educate her. And that meant commemorating the moment she touched the Bean for the first time.
I think people underplay Chicago's prestige and reputation as a great city of America. The first two places are usually reserved for Los Angeles and New York, and it's easy to see how competitive the third slot is. But Chicago is a proud and beautiful city. Its urban environment and the overall resilience and cooler attitude of its people reminds me so much of the Big Apple. But its denizens are kinder. They may grit their teeth in annoyance if you don't know what you're doing, or shoot you a curious glance if you seem out of place, but they'll also drop everything to rush out of a coffee shop to aid a woman yelling for help. They'll see you again in your local spot and give you a genuine, welcoming smile. It might just take a couple of times before you get there.
I'll be back Chicago to explore you further! But so long for now the Windy City~
Obligatory photo dump:
