To say Chicago was everything I expected would be an understatement. I’ve never been to a city larger than Grand Rapids or Detroit in my twenty-year life and I have always dreamed of going to one. I imagined what it would look like and that everyone there would be fabulous. I imagined they were all living amazing lives, where they would wake up in the morning and get a coffee on their way to a glamorous city job in one of the high-rises and have a cute little apartment and go to swanky bars and restaurants every night. While some people probably do that stuff, there is so much more to the city than that.
My mom, a family friend, Cindy, and her daughter, Emily and I left mid-Michigan for Michigan City on Thursday afternoon. I was so excited because the fact that I was going to Chicago finally felt real. I couldn’t wait to see if Chicago was everything I had imagined it would be. Although, when I thought of a big city, I also thought about New York. I mean, for a self proclaimed Fashionista like myself, that seems to be the ideal; the Holy Grail city. The place everyone wants to be and work and live. So I wondered if Chicago would be like what I imagined New York to be like. If that even makes sense.
That night, we all went to the cutest Mexican restaurant ever. We were on the lookout for an outdoor patio to sit at and it was the first one we came across. I mean to be honest, we are all Mexican food freaks, so it was the perfect fit. After stuffing ourselves with chips, tacos and burritos, we made our way to Lake Michigan. Even though it was freezing, we walked the beach and relaxed before we headed into the city tomorrow.
The next morning we took the train from Michigan City to Chicago. It was an hour and a half ride and I was just enjoying looking out the window. Watching the cities change and zoom by was exciting to me for no other reason than that my surroundings weren’t filled with trucks and dirt roads. I have recently felt so trapped in my pretty typical, boring, small-town life. I mean, besides work, I don’t have any other responsibilities. Being summer and all, school isn’t a worry. And although I always have great plans to spend my free time doing something fantastic, I always end up watching endless YouTube videos and TV shows, wishing I was living someone else’s more interesting life.
After getting off the train to the underground station at Millennium Park, my excitement was at an all time high as people rushed around me. Most of them were probably visiting for the day or going to work. A few had suitcases like us. After taking a much needed bathroom break, we ascended the stairs onto the downtown Chicago streets. I was immediately met with skyscrapers that I had only seen in movies and music playing from some street performers. I immediately fell in love. There was just so much to look at and as we made our way to the Hyatt Regency where we were staying, I tried to take in as much as possible. I just loved that the atmosphere was electric and full of life.
Settling into our hotel was easy and our view was partly of the city and partly of the water around Navy Pier. We were only on the eleventh floor, but because I had never been higher, I didn’t mind. We didn’t have any specific plans, so we simply walked around. I wanted to go down every street and see what was there. I loved that there were huge clothing stores and small shops right next to each other. There were restaurants I’ve never heard of before and ones I had. There was quite literally a Walgreens on every corner and buildings I didn’t know what was inside.
Cindy and Emily had been to Chicago multiple times and wanted to eat at a rooftop restaurant they had been to before. It was a very hot day and if you know me, you know I don’t fare well in direct sunlight, unless I’m at the beach. The rooftop was crowded, but the environment was cool. I was appreciating that people were everywhere I went and I didn’t mind just observing them. After snatching a table with an umbrella for some much needed shade, we ordered. My mom and I split a chicken quesadilla and an avocado chicken sandwich. Oh ya, and the biggest piece of carrot cake I had ever seen. Some guy even came over to take a picture of it. Everything was delicious and my taste buds were in satisfied bliss.
Right after lunch, we walked more, coming across the largest Forever 21 I’d ever seen. I had wanted to save all the shopping for tomorrow, but I simply couldn’t resist. Walking in was so overwhelming. I aimlessly wandered around, gravitating to anything that caught my eye. Thankfully, I was too shocked at the size of the place to grab much to try on. I say thankfully, because the line for the dressing room was out the door. When I finally got to the front of the line to try on my one pair of shorts, I was in awe of the dozens upon dozens of fitting rooms. I know that’s such a silly thing to be impressed by, but I had never been in a dressing room so big. I probably should’ve waiting until the next day to shop like I had planned though, because as I left my room, I slipped and fell on one of the number plates they put outside your door. They were clear and because of the chaotic state of the store at the time, there were a couple scattered on the ground I never saw. So after bruising my knee and discovering the shorts I wanted were too big, I was ready to leave.
One thing I never imagined about Chicago was the street performers. That same day, we came across a man painted head to toe in silver. He danced anytime you put money in his bucket and I of course got my picture with him. The coolest experience with street performers was after my mom and I went to the top of the Marriott downtown. As we were walking back to the hotel, I spotted a circle of people surrounding something. A group of four or five guys were putting on a show. They would crack jokes, dance and do stunts and flips. One guy even flipped over 7 people at once!
I think that was one of my favorite things that happened the whole trip, simply because it was so unexpected. Something like that would never happen where I’m from. I loved that there was always something happening or something to do. Back at the hotel, my mom and I collapsed on the bed, with our feet aching. We all needed a break before going to Navy Pier later that night.
Navy Pier was very cool. I wouldn’t say it was my favorite part of the trip, but I liked how it was such a different environment than the downtown area. There were birds everywhere and we got to walk around part of the lake and see sail boats on our way there. A lot of the pier was under construction, much like the city, but I loved being by the water. We all got ice cream cones and sat on the boardwalk to eat. It was nice to sit and observe the people walking by. People watching is one of my favorite past times. On our way back down the pier, we stopped at a stain glass museum. It was truly beautiful and greatly unexpected. This is when I noticed how relaxed I was. I had not a stress in the world and I was so thankful that I was there.
That night we were all in bed pretty early. We were lying there, talking about our day and showing each other the pictures we had taken. I would also like to point out that the bed in our hotel was the comfiest thing I have ever slept on. I don’t think I had slept that good in a long time. My mom and I had decided to get up early the next morning to scope out a coffee shop. Even though it was super early I felt refreshed and ready to take on the day.
My mom and I didn’t even bother showering before getting our coffee. We may be addicted, not going to lie. We turned down a street right off of where our hotel was and came across exactly what we were looking for. Inside was small and cozy; something I had always imagined as a tucked away secret in any big city. We got our coffee and a small morning snack and continued walking the city, which is surprisingly quiet at 7:30 in the morning.
One thing that I discovered about Chicago is that it’s a very healthy place. When my mom and I were getting coffee, most of the people we saw were running or carrying a yoga mat. The city also had lots of rental bikes. And when we went to the bean later in the day, there was a huge work out session going on at the park. It was something I never would’ve associated with any big city. A second thing was that everyone we ran into was so nice. You always hear of people in New York being closed off and not wanting to talk to anyone, so I just assumed Chicago would be the same way. But it is so different. Maybe everyone was kind because it’s in the Midwest? This openness sometimes went a little overboard. On our way to dinner later in the day, a women from Israel asked me if her texts made sense. English was her second language and she was texting some guy she had met online. No big deal right? Then as we left the hotel with her still chitchatting, she asked if I could take her picture. I still didn’t find this weird at all and took a shot. She ended up wanting a full blown photo-shoot because she didn’t think she looked young enough in any of the pictures. She even began asking my mom and I for advice on what she should say to this guy she was about to meet for the first time and if her outfit was sexy enough and what she should do when she had to leave in a week. Thank god she was headed somewhere else than we were and eventually left. Lastly, I noticed that every single building had a revolving door. I don’t think I had ever used one before going to Chicago and it felt weird to use a regular door after we left.
Finding our way back to the hotel after our morning jaunt, my mom and I took our showers and got ready for the day. I decided to wear significantly less makeup because it was so hot and quite the hassle to deal with. Today was our only full day in the city and I was ready to make the best of it.
Cindy, Emily, my mom and I started our day by walking to the fountain and Bean in the park. We had gone the day before, but wanted better pictures. After leaving the Bean and Millennium Park, we stopped at any stores or shops that peaked our interest. Our first destination was a Designer Shoe Warehouse. Shoes are my mom’s weakness. She and I both found a pair to buy. We then found a Nordstrom, a Nordstrom Rack, Barnes and Noble and a couple of malls. One store I was the most excited about was Akira. My friend Nicole told me I had to go there because it was only in Chicago. Let’s just say she was right. The moment I walked in, I saw a billion things I liked. They were playing Ciara and Destiny’s Child and one of the workers greeted me like, “Hey girl!” It was my kind of place for sure. I was pleasantly surprised that my mom even found something. She fell in love with this hand-beaded clutch. Although it was expensive for a purse she didn’t have any reason to wear, she couldn’t resist. And that’s okay. We both reasoned many times that day that, “We’re in Chicago! Buy it.” She even surprised me by buying a woven clutch I had my eye on to commemorate my first time in Chicago.
I also hit up the Burberry store. Not because I really wanted to buy anything, but because I’ve heard the employees judge you hardcore. So I waltzed in and went straight to the makeup, my weakness lately, and a man greeted me. He seemed very nice and I didn’t feel judged at all. I felt bad I didn’t buy anything, but that was my ‘care too much’ attitude coming out.
For lunch, we googled another rooftop restaurant. We had good luck with the first one, so why not try another? The one we came across was even better than the first in my opinion. It was covered and surrounded by water misters. Again, the food was fantastic. Probably the best burger I’ve ever had and paired with sweet potato fries, a personal favorite. We all chatted about our day and the trip so far. There was an apartment complex right across the street that we googled to see the price of. It was insanely expensive compared to what I’m used to. We then started discussing the possibility of me doing an internship there, which I was definitely not opposed too at all.
Lunch lasted awhile, but after being refueled, it was time to tackle the infamous Macy’s on State Street. I don’t even know how many levels there were, but it was a lot. Sadly, Emily wasn’t feeling up to it, so her and Cindy made their way back to the hotel as my mom and I explored. I loved the architecture of the store. Many buildings around the city had beautiful architecture that was unheard of around my hometown. Searching the clearance racks, I found a sweatshirt that was 75% off. It was one that you knew was expensive just by looking at it because it had thick, crisp fabric and zipper details. When I went to look at the tag however, it was completely cut off. My mom convinced me to try it on anyway, and after it fit, I had to find out the price. The clerk informed us they were discontinuing that designer from the store, so there wasn’t even a comparable item to look at for a price. She had to find a long sleeve shirt to ring up instead. To my surprise, the top ended up costing $9.99. How that’s even possible when it started at $138, I have no idea. But I didn’t want to say anything and have the clerk change her mind. So I bought the sweatshirt and walked away feeling as though I had stolen it.
My mom and I got back to the hotel for a quick break like the day before. We were all planning on going to get something to eat and then go to the John Hancock Building. Now if you don’t know, Chicago is nicknamed the windy city. I didn’t quite understand why until we started walking to find a restaurant. In a matter of minutes it went from being a calm, warm day, to so windy, I was running for cover. My mom made a beeline to the nearest restaurant, which was a seafood bar and grill type of place. None of us liked anything on the menu, so Cindy and my mom ordered a drink while it started pouring rain outside. We watched as people ducked under nearby awnings to try and stay dry. Even though we didn’t like the restaurant, we got there just in time to not get soaked.
After the rain and wind subsided, my mom and I walked to the John Hancock building as Cindy and Emily went to find food. I was actually getting quite nervous. I’m not a roller coaster person and for some reason I felt like I was waiting in line for a ride. As the elevator zoomed to the 94th floor, my ears popped many times, and excitement set in. We were going VERY high. As we walked off the elevator, the city spread out beneath us. We walked to every window and took in the view. It was beautiful. This is when it really set in that I was visiting such an amazing city. What I was seeing with my own eyes was exactly what I saw on screensavers and postcards. I could see navy pier, rooftop pools, and boats on the horizon. Everything just came into perspective as I noticed what a small part of Chicago I had actually been too. There was so much of the city that was left to explore another time. And guess what else? We even witnessed a proposal!
The John Hancock building had just recently put in a new feature called the tilt. You stood on a clear platform with seven other people and were tilted 30 degrees away from the building’s edge. It didn’t look so bad, so of course I tried it. Boy, are looks deceiving. It was scary at first! I felt like Spider Man propelling off the side of the building or something. But the experience was more than worth it. It was definitely something I will never forget.
Because we still hadn’t had any food since lunch, my mom and I went to a bar and restaurant connected to a nearby hotel. In Chicago, almost every hotel has at least one restaurant connected to it. It felt swanky and somewhere that a native to Chicago would go. Whether that’s true or not didn’t matter to me. It was the fact that in this moment, I was happy. Although my mom and I both agreed it would’ve been better if I was 21, enjoying a glass of wine with her. We ordered calamari and spinach artichoke dip, which I discovered I liked. Although the calamari didn’t compare to Palazzo di Bocce, I gobbled it up.
After sitting and talking for a while, we decided it was time to head back. We jumped into a taxi right outside the restaurant and took it back to the hotel. Riding in a taxi was something I had never done and was the last thing on my Chicago to do list. Our driver was foreign, but said he had been driving a taxi for nineteen years. The feeling of zooming through the city at night was amazing. Because we had walked everywhere, riding in a car was such a different experience.
Back at the hotel we greeted Cindy and Emily, who had been back for a few hours now, and told them about the things we did. Out of nowhere, we hear small booming noises coming from outside and look out our window to see fireworks. I don’t think we could’ve had a better view from our room as we watched them shoot off over the water in all their colorful glory. It was truly one of my favorite moments of the entire trip, because I felt as though the city was saying its goodbye to me. Given, I think there were fireworks every Saturday night, but I didn’t care. It was the perfect ending to a perfect day.
The morning came too fast and the last thing I wanted to do was leave. We packed up our stuff and rolled our suitcases back to the Millennium Park train station where we had been two short days ago. My mom and I stopped at the Starbucks for some morning fuel (sorry Biggby!) as Emily and Cindy went to Burger King. As we waited for our train, it still hadn’t set in that I was leaving this amazing place. We boarded and took the hour and a half train ride back to Michigan City. We then got back into the car and drove home.
I still didn’t feel like the trip should be over, but I was so content that I even got the chance to go. I loved every second of the weekend and it was as amazing as I had hoped. Chicago is truly a special place that I hope to visit many more times in my life. Who knows? Maybe I’ll get an internship there. Maybe I will live there. Maybe I won’t. That’s the crazy thing about life; you never know where it will take you. Regardless, I am happy I had the chance to finally experience a big city with people that I love. And my most important discovery? Finding out a small town girl like me can survive a big city.
Cinnamon & Chiffon 