Oh man, WHAT A WEEKEND. It’s fun to start at the beginning, right?

Gina and I booked our tickets to Chicago in early January, meaning we planned this trip three weeks prior to us flying out. It was the shortest trip I’ve ever been on, and most of this trip happened way too fast for me to remember everything clearly. But I am going to do my best to document it because Chicago was hands down one of the best and funniest three days of my life.


We arrived in Chicago at 8pm on Friday, January 29th, and it was cold for us California girls! But we braved it anyway, taking the public transportation system like champs before turning in our champ cards and ordering an Uber. I remember stepping out of the bus and into the beauty of downtown Chicago— what a sight! It was like New York, but less polluted and crowded, yet still so beautiful with all the skyscrapers, people dressed in scarves and sweaters, and coffee shops left and right. My favorite feeling in the world is taking my first step into whatever new city I am in. I’ll never forget the moment I stepped out into New York City after the 1.5 hour subway ride; my heart was literally skipping! I must have looked so ridiculous with the huge smile plastered on my face. But Chicago was no different; it made me feel jittery and oh so excited inside. After our Uber dropped us off at our hotel, the pizza guy (yes, Gina and I ordered pizza while on the bus so it would be ready by the time we got to our hotel, don’t judge) had JUST arrived, it was literally perfect timing! So… this is the part where Gina and I are like “eeeeeek” on… Gina has this incredible friend named John who has multiple restaurants in Chicago… and so when Gina asked for recommendations of what to do in Chicago, he was generous enough to book us our hotel… at the Langham. Which is across from the freaking Trump. Do I need to say more??

It was the nicest hotel room I’ve ever stayed at. It overlooked downtown Chicago, had a bathroom fit for a queen, and there was a complimentary bottle of wine and a cheese plate just waiting for us like it was no big deal. After spending 5 hours on a freaking plane, IT WAS A BIG DEAL. We gulped the wine, devoured the cheese, and basked in the best deep dish pizza I will ever have in my life. It was too good. JUST TOO GOOD UGH I MISS IT SO MUCH.IMG_7614

So after we were done squealing over the amazingness of our hotel room, we got ready for our night on the town. At this point, you’re probably wondering why Gina and I went to Chicago. Well, your guess is better than ours! Okay, not really, but Gina and I are in our last year of college and we figured since at the time we were in syllabus week (the semester had JUST started), why not make a weekend trip to Chicago? Tickets were cheap, and we’ve heard nothing but amazing things about the city. Gina and I have a passion for traveling, and we’re eager to check off different cities on our list especially while we’re young. We wanted to have a weekend of fun, and Chicago just seemed to be calling our name. So this trip was definitely spontaneous but I’m so glad we did it.

So after we got done getting ready, we set out to experience the Chicago night life! We first went to a bar/club called Howl at the Moon. The bouncer checked our ID’s, asked why California girls smile in their photos, and after paying a $10 cover charge, we were in! We immediately went to the bar where Gina turned to me and said “We’ll figure out the money thing later?” which was music to my ears. We ordered a Sex on the Beach, which was served in the long plastic tube thing, and paid our bartender 20 bucks before happily sipping on it while finding a table to sit at. Can you just imagine? Two asian California girls sipping on the whitest white girl drink ever in a bar of predominantly white people? I wish there was a picture. Anyway, Gina and I didn’t sit for long because these two guys sitting a couple tables away called us over, where we introduced ourselves and told them where we were from. Gina went off with one of the guys as I talked to the other, who’s name was… Kevin (?), and a minute later, Gina came back with a bucket of alcohol. Yes, you read right. A FREAKING BUCKET. As the four of us sipped from this bucket, I was definitely feeling the alcohol. Kevin asked me to dance, and I agreed, and I’m literally laughing as I type. I never danced with a guy who had moves like Kevin… he was doing these movements that I’m literally too embarrassed to type out. He was practically…. snaking around me, just while standing up. I was drunk, but found this to be the most amusing thing I’ve ever experienced. He was so into it! After showing off his killer dance moves to me, we headed to the bar because clearly I needed another drink. He bought Gina and I a Gin and Tonic, that I remember, and he got upset when these two guys came up to us. I also remember us sharing a taxi with Kevin since we were headed to the same area (he lived two blocks away from our hotel) and Kevin mentioned “It smells like pizza in here” in which I agreed, and then Gina goes “That is not pizza; that is some Mickey D fries.” And the taxi driver turns around, red Mickey D’s fries cup in hand, asking “You want some, girl?!” When I woke up the next morning, hungover and sober, I died of laughter from that faint memory. Gina and I didn’t get back to our hotel until 4 am, WHERE I FREAKING RIPPED MY CONTACT. AND I DID NOT HAVE AN EXTRA PAIR. So I was basically blind for the remainder of Chicago.

Lets skip to that part! The morning. Gina and I woke up, reminisced about our memories of last night (technically that morning), and got ready for our day. Our hotel had a complimentary breakfast for the VIP guests, which John made sure we were, so we had breakfast at the top story of our hotel overlooking all of Chicago. I kid you not, this breakfast was better than most breakfasts I’ve ever had. We had it so good in Chicago.


After fueling up, Gina and I went off to explore what else the city had to offer! We ventured off to Millennium Park where the iconic bean is. After we took a million photos, we headed the opposite direction to this cool indoor market where we had delicious gelato! We also stopped at at a doughnut shop owned by John where we got these huge delicious doughnuts and typing this is making me wonder why I’m not sinking my teeth in one of those bad boys, sigh.




We headed back to the hotel to enjoy our complimentary lunch, which once again, was the best hotel complimentary lunch I’ve had.IMG_7726 IMG_7740So…. this is the part where it makes me cringe to talk about. I haven’t even really told people about this part ha! Basically… IbookedmyflighttickethomeforTuesdayinsteadofSundayandwasfreakingout. Phew, it felt good to let that out lol! But yes, I accidentally booked my ticket home on the wrong day, called the airline to straighten it out, and 130 bucks later, I was angry, pissed, and on the verge of tears. So what did I do? What any 21 year old would! Gina hesitantly watched in amusement as I took advantage of the open bar at our hotel, poured myself a nice big glass of straight whiskey, and started sipping like it was going out of style. I know it sounds like I’m an alcoholic— but I swear I really only drink when I’m on vacation! Once I was buzzed enough to where 130 didn’t seem like THAT much for a broke college kid, we went to Sears Tower which is one of the highest buildings in the US. Check out this awesome photo we took!IMG_7768

After that, we went back to our hotel room where Gina made me a nice, strong Gin & Tonic and I gulped that down too. Once again, Gina watched in amusement. Even though my dumb mistake left a sour taste in my mouth, I was going to make the most of my last night in Chicago. I was determined. Being blind and 130 bucks out was not going to stop me.


So we called an Uber… and this is where the real adventure begins. We had the most frightening Uber drive of our life, and got to our destination in 40 minutes where our app told me 20… So you bet your bottom dollar I emailed Uber and demanded a refund. We explored Wrigleyville which was literally white men central; I was in heaven! But none of these bars appealed to us. Gina and I had no idea why… but it just wasn’t popping for a Saturday night! Granted, it wasn’t baseball season at the time, so maybe that’s why, but still. Where were all the cute college boys?! So we decided to order an Uber and head back to downtown, our previous night’s stomping grounds. After another frustrating Uber ride, we finally were in Downtown. This part is where it starts getting blurry (I’ve bet you heard that one before); Gina and I stood in the cold for about 20 minutes until we finally got into this bar that I can’t remember the name of. The whole night was getting to me; our uber drivers, my lack of sight, being out 130 bucks, standing in lines, the cold, etc., and Gina knew I was in need of quick solution. So what was her solution, you ask?

SHOTS. 4 of them. All tequila. Overpriced. But very much needed even though initially I refused as soon as she ordered them. But she wouldn’t hear any of it, shoving a shot in my hand and silencing my protests. And there we were, two asian girls slamming down shots of tequila like we were 40 year old Mexican men. Even the middle eastern men behind us were impressed. SO. Tequila did the trick, and I was definitely buzzed. Buzzed enough to where I found it totally acceptable to wait HALF AN HOUR in line in 35 degree weather to get into some random club across from our friendly Tequila place. During that time, one of Gina’s friends met up with us who goes to Perdue. He drove two hours just to meet us in Chicago, how nice is that? BUT WAIT. IT GETS NICER. After we got in the club, in which my initial reaction was, “I waited half an hour in line for THIS?”, he bought Gina and I all the drinks we wanted! What a gentleman, #amirite? So all was well and dandy for Caroline who was happily sipping on her Jack and Coke! And then I found a group of fun girls, who were all white so of course I stood out like a sore thumb, and we danced the night away as I laughed and giggled and told them all how beautiful they were. And then all of a sudden No Scrubs by TLC came on and I literally felt like I was on cloud nine. I had my favorite alcoholic beverage in hand, dancing with random girls who were so so nice, and I was in FREAKING CHICAGO; all of the trouble I ran into was so worth this trip, especially with my jam playing in the background! After that, I found Gina, mentioned I was going to go buy another drink, and her sweet friend went and bought it for me. And that’s when I met… We’ll call him Jake, because that’s what my best friend Nick says he looks like. Funny story, I was actually talking to Jake’s friend, because Gina encouraged me to in which I SHOULD NOT HAVE, because he was not my type at all (I blamed it on my inability to see and gina’s drunk judgement). BUT. Even though I was blind, I turn around and was faced with what I would consider my “ideal” white guy in terms of looks. Good ol’ Jake was tall, had brown hair, clean cut, blue eyes, and a cute smile, UGH. HE WAS SO CUTE. And of course, that liquid courage I was gulping two seconds earlier gave me the confidence I needed to introduce myself to him, but then I don’t remember what happened next because I was dancing with those girls again. And then Gina came up to me, mentioned she would be right back, and somehow all of a sudden I was with Jake and we went to the dance floor and started dancing and telling each other how cute we thought one another was. Or at least I think that’s what happened. But I don’t remember much, so please don’t take my word for it. Drunk Caroline is on another level when whisky is involved.

To make a long story short, I went back to the hotel at 5 AM. Gina had already went back to the hotel and I discovered this before I hopped into my Uber; poor thing wasn’t feeling too hot and her phone was about to die. I agreed to meet her back at the hotel with the 1% left of battery she had to spare on her phone when she texted me, and plus everywhere was already closing. I decided to go to the top floor to get breakfast, and I’ll never forget that moment. I was eating by myself, overlooking Chicago, thinking: “This is incredible…

Why do I have to be drunk?”

Guys– I was still intoxicated. At 6 AM. In the nicest hotel I’ll probably ever stay at eating a complimentary breakfast that I did not deserve. Realizing this, I went back to our hotel room where Gina croaked out “Did you just get back?”. Exhausted, I nodded my head, and she shook her head in disbelief. She offered out her fist, where I met it with mine, a silent but mutual agreement that we handled Chicago like champs. And then I crashed for the next hour before Gina  shook me awake saying we were going to miss our flight if we didn’t leave NOW. So I threw on clothes, said goodbye to the most incredible hotel room, and we jetted off to the subway praying that we’d make our flight. We almost didn’t, but the flight Gods must have taken pity on us because we made it just in the nick of time. So there I was, on a plane, drunk enough to struggle when taking off my seatbelt, sober enough to understand that I was going to need a serious detox as soon as I got back to San Diego.

SO. To sum it all up, Gina and I slept a total of 6 hours in our 36 hours in Chicago. I was blind for 75% of the trip. I was out 130 dollars. I don’t remember a lot of it. We almost didn’t survive it. And yet…

Gina and I still classify our 36 hours in Chicago some of the best 36 hours we’ve ever spent.



p.s Follow my blog with Bloglovin!

Leave a Reply

Your email address will not be published. Required fields are marked *