Soloing Through Thanksgiving: Welcome to Chicago! (1/3)

Day 2
Day 3

2015 is the first year that I moved out and lived on my own. For those who haven’t been following my blog, I moved out to northern San Diego, from Hawaii, for work after having graduated from the University of Hawaii last year. Naturally, flights back home for such a short holiday were unfortunately quite expensive: nearly $900 just for four days! Flying back was not an option, especially considering that I had already booked my flight back home for December, for a fat three weeks at that too.

In addition, this is the first year which I’d spent my Thanksgiving away from home. And it wasn’t too bad. Not too bad at all.

Thanksgiving is definitely the holiday of the year to enjoy that quality time with the family. But if the circumstances don’t allow it, it’s the longest holiday of the year barring Christmas and its eve, so might as well take advantage of it!

About three weeks before Thanksgiving, I bought myself a spontaneous one-way ticket to Chicago. Why Chicago? A simple Google search of places to go during Thanksgiving piqued my interest in its McDonald’s Thanksgiving Parade. New York’s Macy’s Parade was unarguably the top parade, but my introversion of going solo to a parade with three million spectators was telling me I wasn’t quite ready, especially as a Hawaii kid dealing with such extreme climates. Chicago was a nice middle ground, not having visited the Midwest before (except once, but I was only 9 years old and didn’t recall anything) and having a popular but not so overcrowded parade to enjoy on my own.

One-way ticket? I wanted to visit somewhere on the way back, thinking I could cover the major tourist spots Chicago had to offer in two to three days. Planning a multi-city trip, say from Chicago to Texas to San Diego, would have been around the same price as getting a direct flight. Where I wanted to go, I wasn’t quite sure yet.

A week passed and I had to make my decision immediately; two weeks is generally the deadline to book flights before prices soar as high as the planes themselves. I just couldn’t decide! So I thought about my previous blog posts, and I ended up, also on a whim, purchasing an Amtrak train ride all the way back home!

So in this post, a recap of my nontraditional experience soloing through the traditional family holiday.

Day 0, Tuesday

I was fortunate enough to plan ahead with my supervisor at work to work an exhausting week the week before, pulling out somewhere between 60 to 70 hours including Sunday, on a typical 40-hour office job. Partially because I could take the Wednesday before Thanksgiving off without using a vacation day, but al

so working beyond 48 hours because of a project deadline being that Friday before. It felt like cheating the system, having worked a “full work week” by working only Monday and Tuesday, but once 5pm Tuesday hit, I fled from work to catch the train to the airport in time. A train and two bus rides later, I get to the airport around 8pm and relax beyond the security gate, waiting for my 9:30pm flight.

On boarding my first flight, I happened to have been walking right behind a guy sitting in my row. A woman was already sitting in his seat, getting the letters for the aisle and window seats mixed up, so as the man told the woman about the situation, I smiled thinking that all three of us just happened to be together just like that. The man allowed me to walk past him, but I told him I actually had the middle seat, and conversation ensued from there, among all three of us for most of the hour-long flight.

The man was as quirky as he was humble. “I guess we’re all stuck here together for the next hour!” He was a modest bicycle shop owner who wished he could travel more, but was making the time of his holidays to go back to his home in Michigan.

The woman was as powerful of a lawyer as she was experienced of a traveler; it was amazing hearing her stories of balancing these parts of her life. She took advantage of every holiday, traveling every time the weekend was longer than two days. Her lawyer side told us stories of her supervisor “quitting” right before she got fired for fraud within the company, giving up a salary of over $180,000. Her travel side included Argentina, Jamaica, Bali, China, Egypt, and a plethora of states that I can’t even recall. All while having a 40-hour office job, and I would guess that she was in her early 30s. She was not afraid to admit that she spends majority of her expenses on traveling, a trait I admired since I’ve been starting to believe that life is way too short to not travel and experience new places and cultures. I shared with her my limited but developing aspirations of traveling for Super Smash Bros., a new lifestyle that majority of the world isn’t quite accustomed with yet.

As much as I enjoyed the man’s candor, I definitely related to the woman and her lifestyle more, hoping that I would be as well-traveled as her in the near future. Although it was only an hour-long flight at night, it’s definitely one of my most memorable yet.

At my layover in Phoenix, I bought myself an ordinary cup of won-ton soup for the night while charging my phone and picking up a new book: Born to Run by Chris McDougall. I had just started this book while waiting at the San Diego airport, and I was only about 50 pages in right before taking off from Phoenix, but between then I had three people come up to me asking about the book in my hands. One had heard about the book and had only heard great things about it, while having just started up on running. Another was a solid runner but surprisingly actually hadn’t heard about the book. The last person ran as a hobby and read the book ages ago, claiming it was one of the best reads in his life. He later told me how he used to travel in his late 20s to early 30s, now late 30s, just to compete in marathons; after hearing that, I was not surprised. Just by holding a book in my hand I was able to converse with runners from across the US for a solid ten to fifteen minutes each before they each parted their own ways.

The flight from Phoenix was about 3.5 hours and was simply used to get as much sleep as I possibly could. Oh the things we do to save money on cheap flights! Any other flight, nonstop or otherwise, would have cost me at least $100 more, and I was not planning to spend half a day in waking hours simply flying.

I arrive in Chicago around 6am. Still completely dark, but the sun was just about to rise. Good morning, Chicago!

Day 1, Wednesday

A full day laid ahead! Unfortunately, my phone addiction led it to be around 60% (mostly from trying to figure out last-minute what to do in this city!), so I spent the first 45 minutes or so just waiting for my phone to charge while eating a quick breakfast and continuing on with my reading. Once my phone hit around 85%, I figured that would be enough to explore this new world, at least for a day.

Around 7am I left the airport via Chicago’s highly efficient rail system, the  CTA’s (Chicago Transit Authority) ‘L’. Each ride is $5 a pop, but I bought myself a 3-day pass for only $20, which in comparison was such a steal. The blue line provided a direct connection to and from Downtown Chicago, which took just about 40 minutes.

I got off at the “Loop” of Downtown, familiarizing myself with the entirety of this system. It was a lot to download, but yet it was fairly straightforward, especially with Google Maps complementing the L quite well. I next had to catch the pink line, headed for my AirBnb room at Little Village just to drop off my clothes. This ride was about 20 minutes, followed by a five-minute walk, ten including getting just a little bit lost.

I had just messaged the host the morning before if I happened to be able to drop off my bag in the morning of, mentioning that if it was not possible then I’d be more than fine following the expected 4pm check-in. Even with this request being last minute, she was perfectly fine with it as she had minor things to take care of around the house at the time anyway. We messaged back and forth the day before, and from that I could tell that she was going to be a great host. When I got there, she was extremely kind with getting me accustomed with the room, the house, and the city. This was also a community room where I shared a room with three bunk beds, so she introduced me to one of the roommates who was there and awake. Everything was rather grand, and I was only paying $15 a night.

It was almost 9am; it’s about time I truly start my adventure! It was a rather sunny day despite the forecast, so I started off by visiting the Lincoln Park Zoo. Being too stubborn to catch the bus because of my rail pass, my transportation time from my room to the zoo was about an hour including 15 minutes of walking, compared to potentially 40 minutes. The residential houses I was passing by were very reminiscent of a typical American neighborhood in the autumn season, oddly something I hadn’t seen before, being a Hawaii kid. Grabbed some nice photos here and there while walking in around 45 degree weather with comfortable winds.


The zoo itself was rather barren, but the scenery was amazing. I wasn’t accustomed to the animals being able to walk between an indoor and outdoor setting, and most of them ended up inside due to the cold weather, but I was first stunned when I saw almost nothing living at first glance. On top of that, Christmas lights were set up everywhere, but nothing was on. Not too many people were walking around. Navigation around the zoo was rather odd with having to back-track several times. I wondered for a moment if the zoo was really worth all of its hype on Yelp. However, the scenery itself, plus some unique animals I’ve never seen before (not even in other zoos), made the trip to this zoo worthwhile. In addition, free admission! Great diversity, of birds, fish, barn animals, and everything you can think of. Walking along the zoo with the cityscape in the background was rather interesting as well, especially given how accurately they created these habitats. The trip here lasted a good three hours or so.

Highlight of the zoo experience was watching a male African lion roaring after having jumped up onto a cliff at least 50 feet high!, claiming its presence toward two female lions who laid at the base.


Given lunch time and my tiring legs, I decided to look up Yelp to see where nearby I should grab food. I happened to have been just two minutes away from this French place with plentiful ratings, so I checked out Bistrot Zinc. I ordered a rather interesting dish: Risotto with beets and oxtail, one of their specials. The beets made it so unique, both in looks and in tastes; I was eating a rather sweet purple dish! While I enjoyed the dish and the experience, the butter and cream of the risotto made it rather heavy, and I probably wouldn’t get it again. For dessert I ordered the Berry Mascarpone, aiming for something light. While the mix was fantastic!, I think the mix of the mascarpone cheese with the risotto made my stomach act up QUICK; after only having finished a quarter of the dessert, I headed to the bathroom immediately. Regardless, my food addiction forced me to finish off the goodness that is desserts afterwards.

My next stop was at 360 Chicago. As the name implies, it’s a skyscraper with a full 360 view of Chicago. I bought myself a CityPass there as well, planning to visit five attractions including here for about $100 given a $200 value. The views were definitely amazing, being able to see the zoo I just visited, the beaches, downtown, and everything in between! However I don’t think I’d pay $20 just for that if I knew what I was getting. The sheer name of it being a big tourist attraction got to me; just another thing to cross off that bucket list.


From there, I walked down the Magnificent Mile, headed to Downtown without not too much of a plan for what to hit up after. I actually hadn’t heard of the Magnificent Mile, but 360 Chicago happened to land right along that street, and the street signs made it sound like a worthwhile tourist spot. It’s basically a huge mall, but since I’m not much of a shopper I just walked down the mile. The architecture you come across, the Christmas and city lights, and the sheer culture vibe you get while walking made it worthwhile.

Two people even interrupted me asking if I wanted to take $5 from them for the Christmas holidays. I spotted them recording me (I even habitually said, “So I see you recording there!”), so I knew something was up, so I instinctively responded, “Sure, under one condition… you accept my $5. Happy holidays!” They said after that they were just filming to see how many people were willing to stop, since they were holding out a cup making it look like they were asking for money instead, with the $5 being their reward for taking their time. One thing’s for certain: it’s definitely hard to think straight once you you realize you’re on camera.


The end of the Magnificent Mile led me to the Navy Pier, the boundary between Chicago and Lake Michigan. If you search “Chicago things to do” on Google, this is the first result. The pictures were stunning, with aerial views of a packed pier that even has its own Ferris wheel! Of course however it looked better in pictures than in person unfortunately. The pier was just as barren as the zoo, with at most maybe a dozen people walking along the pier just to sightsee. Turns out that even the mini amusement park that the pier is known for (the pier’s main symbol is its representative Ferris wheel) was closed! The entire pier is apparently going through a “transformative project” to become greener and more contemporary. Inside the building at the pier was basically just another mall, with not too much to say about it. It has its own movie theatre and a large array of food places, as well as a Children’s museum, but nothing really of interest for me. The sights outside were definitely worthwhile though, despite the incoming clouds.


Now a bit past 4pm, I decided to head out back to Downtown, thinking about checking out the parks. About a 20-minute walk away, I continue down the street of the Magnificent mile, following my phone to Millennium Park and Maggie Daley Park. My goodness, was THIS a sight! I started off by checking out the Maggie Daley Park, since going to the direction of Millennium Park was on the way to the rail system. The biggest attraction at this park was an outdoor skating rink called the Skating Ribbon, where people can skate for free (but with skates rental fee of course). The ice-like sculptures made it such a grand park that all I was thinking of was, “Dang, the little kids have no idea how grateful they should be for living here!” Maggie Daley Park also had its own rock-climbing wall, playground, and overall nice scenery all around.

A contemporary bridge made of a multitude of stainless steel panels connects the two parks together. Millennium Park was even more amazing, and I thought Maggie Daley Park couldn’t get any better. Millennium Park basically makes Chicago look like a contemporary architect’s dream come true. All of its statues, sculptures, and structures together (and Millennium Park also having its own skating rink, but not nearly as fancy) made this probably the number one park in the US. Of course nobody can forget the Cloud Gate, aka The Bean, claiming itself as the number one contemporary sculpture thanks to the selfie obligations. There was just so much to explore among these two parks that I had only really finished seeing everything after nearly two hours.

Since the holiday season was approaching as well, there was a huge 63-foot Christmas tree towering over everyone, right next to the ice rink. This made me realize that I was truly grateful for everything in my life, from what my family had provided me to what I had gone through to be able to live this experience, missing my family and friends in that moment. I stayed near the tree for a solid fifteen minutes or so, just letting these thoughts run as I collected myself (and let my feet recover!).


Right across the street was the famous Shake Shack, which I thought was only in New York and Las Vegas this entire time. I had tried a shake in Las Vegas, but I hadn’t actually tried their burgers before which they were truly known for, so I gave this place a shot. (Side note, apparently this location only opened up back in May 2015.) I got myself a double Roadside Shack, which is a burger with two patties, double cheese, bacon, and caramelized onions; on the side, a Fifty/Fifty, half lemonade, half tea. Good, but overly hyped in my opinion, but that may just be my healthy side speaking.

Halfway throughout my meal, I found a woman similarly eating by herself, with a vintage camera. She seemed to have been in a similar situation to mine, so I decided to go up to her and ask her all about it. Turned out that likewise she was alone for the holidays, actually working and living in Chicago but this year being her first year here. She showed me some of the pictures she took, both of the nearby area during that day plus a plethora from before, and simply seeing all these photos throughout Illinois was absolutely stunning. Likewise I exchanged views, showing her pictures I took of that day while telling her my story of how I ended up in the Windy City. I’m not used to approaching people just like that, but I definitely don’t regret this one time I did.

Unfortunately, I actually had to cut my time with her short, as I had wanted to check out an event that was quickly approaching. What event? None other than a Smash tournament! Apparently Wednesday nights are Chicago’s biggest weekly tournaments (and this was really the only thing I cared to plan for beforehand, trying to find the Chicago Smash Facebook group and everything!), so I ended up at the right place at the right time. This was only about a 30 minute train ride + walk away. I got there, told everyone I played that I was visiting from Hawaii (not Socal, since nobody can really represent Hawaii), and took quite a bit of names! I talked most frequently to a player whose highest rank in the Chicago power rankings was 5th, and was winning just a bit more often than not. The one thing I do regret however was that I was unable to give them my best at all; I just didn’t have enough sleep to function mentally. I won about 5 matches out of 50 people, putting me around top 12, but sadly almost all of my deaths were simply because I killed myself! Regardless, everyone thought I was an amazing player, and I definitely put Hawaii on the map! Still disappointed with my losses, I left the venue rather early (around 10:30pm when the venue closes at 3am), both to get away from my disappointment and to finally get rest for the next day – it was gonna be a long ride back home.

Having fallen asleep on the train multiple times throughout two routes, I was truly exhausted. My legs had been killing me as I walked around literally all day, from as early as 7am to almost midnight. I know I walked at least half a marathon’s worth, and more was to come the following day. I took a quick shower and immediately hopped into the bed, not talking to any of the roommates since they were all already asleep. I laid in bed reminiscing about the day: all the sightseeing, the gratitude, the Christmas tree, the lack of sleep and losing to myself; it was definitely a lot to take in. At the same time, my body was clearly screaming and telling me to go to bed, since I swear my legs were emitting more heat than your typical summer day in Hawaii. I was only able to think about everything for a mere five minutes or so, and I fell into the wondrous world of adventure and imagination, just waiting to be unlocked the next day.

Day 2
Day 3


Author: Kevin Who

Developer. Designer. Smasher. Reader. Creator.

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