A Trip to the Windy City

Chicago, IL, USA

I've wanted to visit Chicago for the longest time. I remember almost planning on going with my college roommate for Spring break in Freshman year before we realized we were both too broke. But  I was finally able to visit with my mom and my brother for five days in August, just about a month ago.

We stayed in the North End and mostly traveled close to the Loop on our visit, playing tourist. I had so many destinations bookmarked on my phone, and made sure to hit as many as possible, though wish I could've eaten more meals in a day since the amazing food options were just uncountable. Nevertheless, here is a list of many of the places I visited on my trip to the Windy City.

Art & Architecture

Lincoln Park Zoo & Nature Boardwalk

We traveled further north to the Lincoln Park Zoo on our first day in Chicago, right after we checked into the hotel and ate lunch. The zoo, located right in the middle of Lincoln Park, was ungated and full of weekend visitors. One moment you're strolling through a park, the next, you're in a small crowd overlooking the pen holding three zebras and two ostriches. I was actually surprised at the size of the zoo, which has free admission. I hadn't been to a zoo for a long time, and it was nice to be able to visit one during my time in Chicago.

Right outside of the Lincoln Park Zoo is the Nature Boardwalk, a gorgeous structure overlooking the South Pond. It was definitely a popular wedding photo spot-- I saw at least three different photo shoots being done while I visited. I had to jump in whenever the coast was clear to take photos, and luckily got a few good shots in.

Dress: Boohoo / Shoes: Rothy's

The Rookery Building

Among some of the most amazing feats of architecture I saw on my visit to Chicago was the Rookery Building, located on 209 S. La Salle Street in the Loop. I had seen the famous staircase in photos before, and was excited to view it for myself. Unfortunately, general visitors are allowed only on the first floor of the building, and in order to go in further, we booked a tour on the morning of our third day in Chicago. The tour taught us tons of interesting details about the architecture of the Rookery Building, and I soon found that the famous view of the spiral staircase was actually from the bottom of the stairs-- not the top. I wish I could have seen the stairs from the top, nevertheless, the sights were spectacular.

The Mural at The Flamingo Rum Club

The Flamingo Rum Club was close to our hotel, so we walked over to see the gorgeous flamingo mural on its outer walls. It was definitely a cool spot to visit, and the mural was an excellent example of some of the amazing street art in Chicago.

Top: Mango (old) / Skirt: Topshop (Similar) / Shoes: Rothy's

Cloud Gate

I couldn't visit Chicago without seeing Cloud Gate, AKA The Bean. It was super crowded there when we visited, but definitely still made my top highlights from the trip. We got to explore Millenium Park and Maggie Daley Park as well, and I loved how clean and modern the area was.

The Art Institute of Chicago

We visited a few museums on our trip to Chicago, but The Art Institute of Chicago was my favorite by far. From suits of armor to age-old paintings and pottery, this place had everything. We stopped by the garden outside too, which had beautiful rows of trees, shedding shadows to the ground and fountain below. My favorite piece in the museum was The Old Guitarist by Pablo Picasso. I remember learning about it all the back in elementary school, and it was surreal to see it in real life. Otherwise, I also finally got to see the famous and most gorgeous staircase at the museum, pictured below.

Top: H&MSkirt: Urban Outfitters (Old) / Shoes: Rothy's

For Views

Skydeck Chicago

The tourists we are, my mom, brother, and I had to find the best view of the city. I had always wanted to visit Skydeck Chicago after seeing all of the photos of the ledge, so we headed there first. Unfortunately, while the view was nice, it didn't meet my expectations, and the entire observatory was overcrowded. We could hardly reach any windows through all of the crowds. The ledge was pretty cool, but it took us probably 45 minutes on a line to actually reach one, and we were only able to be on it for a couple minutes. It was hard to get good photos in that time.

360 Chicago

We were pretty skeptical about whether or not we should visit another observation tower on our trip after our experience at the Skydeck, but we heard 360 Chicago was good and had time to go. We decided to go at night though, to get a different kind of view. The experience overall was so much better than the Skydeck. The view was nicer, it was less crowded, and the skyline at night was gorgeous. I even witnessed a couple get engaged up there. I would definitely recommend it.

Navy Pier

The Navy Pier doesn't quite have views of the city, but I found it to be a nice, scenic spot (and a really touristy one, too). We stayed during sunset, and got to see the firework show late at night, too. It was a good way to spend our first night in Chicago.



On the first day of traveling, we arrived at our hotel around 1:30pm Central Time, meaning it was 2:30pm on our NYC clock, and we were famished. Luckily, one of the staff members at our hotel referred us to the nearby XOCO, a quick-service Mexican spot by Top Chef master Rick Bayless. We immediately dropped off our luggage and headed there for lunch. The food was incredible-- I had the Xoco Salad and shared the guacamole, though I do wonder how good their tacos would have been if I didn't want to be so healthy. The meal definitely made me excited for what other food Chicago had to offer in the future.

Ming Hin Cuisine

On our second day in Chicago, my mom insisted that we have lunch at Ming Hin Cuisine, a Chinese restaurant her co-worker had suggested. It was a Sunday afternoon, so the place was a bit crowded, but we were seated in 20 minutes or so. Believe it or not, this was my first time ever trying dim sum (I've always been too picky to eat it before... a story for another time), and it was incredible. My favorite dishes were the BBQ Pork Baos and Fried Taro Cake. I guess I'm still not sure exactly how it compares to other dim sum, but I definitely enjoyed it.

Big & Little's Restaurant

Cheat day came early when we visited Big & Little's Restaurant in North End for dinner. My mom had seen that it was on Diners, Drives, and Dive Ins, and we knew we had to go. The small joint was classically decorated, and I loved the bright diner vibes it gave off. My mom and brother both ordered Porkbelly Po'Boys and a Carnitas Taco, and we got a round of Truffle Fries for the table. I ordered the Deep Fried Grilled Cheese, the most intense grilled cheese I've ever had in my life. The outside was crispy and the inside was all melty and... omg. If I didn't have to worry about the amount of calories I was consuming, I would eat here every day. We all left never wanting to eat again, but I wouldn't take that meal back for anything.

3 Arts Cafe at Restoration Hardware

We didn't eat here, but I made sure to hit this insanely gorgeous cafe in the middle of the Restoration Hardware. The entire store was beautiful, and my mom and I wandered most of it in awe. I'll definitely need to eat here the next time I visit. Anybody want to take me for a date? (A joke, but also not really).

L.A. Burdick Chocolates

I was invited to L.A. Burdick Chocolates during my visit to Chicago and I'm so glad it was close to my hotel and I was able to stop by. It's always such a pleasure to eat at one of their locations-- their chocolate really is like no other. My mom, brother, and I tried a little of everything. My favorites from our spread included the Zuger Kirsch cake, the Caramel Latte, and the assortment of macaroons. I'll definitely be visiting them again back in NYC.

Lou Malnati's 

While in Chicago, we obviously had to try deep dish pizza, so Lou Malnati's was our stop. We went super early, around 5pm, to grab a spot before the wait got too long for dinner. We ordered The "Lou" deep dish pizza and the Chicken Louie, a rich fettuccine alfredo with chicken. Truthfully, I didn't eat any of the deep dish (I'm not a fan of tomatoes), but the Chicken Louie was great. My mom and brother loved the pizza, though, so maybe I have some authority to say this place is a great choice for deep dish.

C.C. Ferns

I woke up extra early one morning to visit C.C. Ferns before my mom's plans for our day began. It was well worth it. The shop was beautiful inside and out, and was furnished with retro decor and music. They served Doughnut Vault donuts too. I got a pistachio donut, which was incredible. Can NYC have a place like this??

Werewolf Coffee Bar

I was really excited to visit Werewolf Coffee Bar after seeing all of the amazing types of lattes they served there. I wish I could've gotten them all, but ended up going for a Sweetbeet Latte, which was perfect for my second latte of the day (I went after visiting C.C. Ferns). The place itself was spacious with a casual ambiance, and I adored the truck that the coffee was served from.

Sawada Matcha

My favorite drink from the trip was probably Sawada Matcha's Black Camo Latte. A blend of green tea and espresso, the drink was not only delicious, but gorgeous, too-- They really create some beautiful latte art there. Even better, they serve mini donuts from Doughnut Vault, which was right next door and had the cutest storefront.

Overall, Chicago was everything I dreamed it would be and more. Even though I was there for five days, I feel like I barely scraped the surface of all of the things I could see in the area. Plus, there's definitely a lot more food I want to eat there. Since our hotel offered breakfast, I didn't get to brunch outside, but that'll just be for my next visit. 'Til next time, Chicago!

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