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  • Writer's pictureBarclay Ann Blankenship

Less Than 42 Hours in Chicago: What I Saw and What I Wish I Had Seen

Updated: Jun 2, 2020

As I'm sure many would proudly argue, two nights and one day is not enough time to explore Illinois infamous city. Chitown is effortlessly cool upon a first impression, especially upon arriving on New Year's Eve when the city is bustling and energetic for 2019. Despite my short visit, I saw and experienced some of wonderful things the city had to offer, both seasonal and year-round.


The strange blurriness of a city at night was draped over the rainy evening as we arrived. I switched frantically between peering out the passenger side window, to leaning over the dash in order to get a better look at the skyscrapers. I knew there wouldn't be enough time to see much of the best parts of the city, and so did my boyfriend, driving, his best friend sitting behind him, and his then girlfriend. The occasion was New Years. We drove from rural Indiana to the city and felt like I was fully embracing the spontaneity of our trip, despite my genuine inability to "go with the flow," or whatever non-anxiety filled people say.


As an avid reader and researcher before new experiences, I quickly became aware of the harsh Chicago winters that we would inevitably endure part of during our excursion. This "research" of mine wasn't impressive, since all you had to do was walk outside, think "Shit. It's cold," then walk back inside to tell your friends to not go outside because it's cold. Between the four of us, all college students, the cost was pretty much at our limit for a one night stay at a Hyatt on the Michigan River, across the way from Trump Tower. Only a short walk from Michigan Avenue, we walked arm and arm across the busy street to window shop in the bitter wind of New Year's Day. But whoa there. Hang on- go in chronological order. I'm getting ahead of myself.


With only half of us being 21, our options were slightly limited to what our NYE festivities would be. The hotel was alive with circulating locals and visitors, like ourselves. With the hotel being so close to the river, the primary attraction advertised throughout the hotel was the city-wide firework show. Our intention was to walk farther down the river, towards the docks, in order to get a wider view of the fireworks and water. However, we were freezing our asses off (refer to paragraph above for my astute weather observations). Our fingers and toes, becoming more susceptible to completely falling off, quickly eliminated this optimistic pursuit from our minds. We were fortunate to find a view from right outside the hotel.


Clutching my over-the-shoulder purse and wrapping myself around the arm of my boyfriend to keep warm, we walked to the 7-Eleven down the street to get gas station-quality champagne to pop in our hotel room after the fireworks. Only classy drinking for us. Even in my heavy coat, bought primarily for snowboarding lessons I took to look like a ~cool girl~, the Midwestern wind bit at my nose and ears still. Soon, we were leaving our hotel once more to eat a quick dinner. Having never eaten deep dish pizza, this seemed an obvious choice. I had considerably low expectations as an adamant thin-crust lover, but was surprised and delighted by the carb fantasy that IS a deep dish pizza. My. God. I connected spiritually to that pizza.


Many city street pictures later, the city firework show was nearing its start. Although they could have been viewed from the comfort and warmth of the hotel lobby, we were in a "why the hell not" kind of mindset and bundled up once more to watch the fireworks in the cold. We nabbed a spot in the center of the street we had used to drive into the city only hours before. After screaming a countdown along with a mass of (probably drunk) strangers, the city erupted into a spectacle of light reflecting off of the buildings and river. The spaces in between the river and the buildings began to fill with a smog from the abundant, erratic firework finale. The street lamps shone through the clouds like fireflies, reappearing for a few moments before disappearing under the blanket of smoke, glowing just enough to light the streets. I remember distinctly not wanting to take any pictures. I wanted to be sentimental and "in the moment." Wishful thinking since my memory is pretty shit most of the time, so I gave in and whipped out my phone to document.


We slept well and tipsy, but woke early the next morning to better our chances of seeing the city in the daylight before we drove back.The bustle of the city was subdued that morning. While most of Chicago was sleeping after a long night of new year celebration, we weaved in and out of the sidewalks down Michigan Avenue. The disappointing reality of exploring any city on a holiday is that many, many things will be closed. Except parks. Millennium Park, home of the Chicago Bean, was our main attraction. the park itself is lovely, with towering views of the surrounding skyline that peeks over the trees. Despite the holiday, it was still busy with tourists like ourselves, hoping to snap a picture or two in front of the big bean. I also flicked the bean without injuring my fingers, as I was quite nervous about that. An accomplishment.


I was left with the most longing to visit the Chicago Public Library. Like many public buildings that day, it was closed. I'm very much the type of person that likes to visit the libraries of new cities. However, we did convince the guys to let us sneak into the American Girl museum for a few minutes to engulf myself in childhood memories and dreams of owning hundreds of dollars worth of doll furniture. They also give you a book with a doll so that was A LOT of good things combined for little Barclay. God bless my sweet mother and grandmother who fueled that doll/book/AG franchise obsession until I eventually phased out of it.


It wasn't a perfect trip, but full of little memories that could have only been created by our lucky combination of being twenty and blindly optimistic, despite our transient stay. In fact, we didn't really do that much at all, but it was exciting to be traveling, reigniting the familiar lightness inside of me that can only be attributed to a new journey. Chicago is worth it, even if for a few days, and I've heard it's even better in the summertime when you aren't so cold that you start to wonder if you'll even really regain feeling in that one toe that's always been funny since you stubbed it. (who? me?) Perhaps I'll find myself there again, and be able to reach out farther-to hold the most beautiful parts of the city in the palm of my hand and carry back the experiences I had left there for another time.














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