Moments in the Windy City
Chicago is a major city located in the state of Illinois, USA, where modern urban landscapes harmonize with historic architecture. Thanks to the unique cityscape created by the Chicago River and Lake Michigan, it is known as the ‘City of Architecture’, offering various attractions such as the Museum Campus, Millennium Park, and Willis Tower. True to its roots as the birthplace of jazz and blues, the music culture is rich, and local foods like deep-dish pizza and hot dogs are a must-try. It is an attractive travel destination where you can enjoy art, food, and architecture in a vibrant city atmosphere.
Transportation / Stay / Weather
We traveled to Chicago during last year’s Memorial Day weekend. We took a flight from LA to Chicago, which took about 4 hours from LAX to O’Hare Airport. After arriving at O’Hare, we took the CTA Blue Line to our hotel, and to catch the Blue Line from the airport, we had to go to Terminal 2. When we first arrived at the airport, the CTA Blue Line signage was not immediately visible, so we followed the signs to Terminal 2, and it was only when we were almost there that we saw the CTA signs as well. A one-day pass could be purchased for $5.
In fact, I decided to use the CTA Blue Line after reading reviews that it is relatively safe to connect from the airport, but perhaps because we were traveling at such an early hour, the atmosphere was quite different. Most of the passengers were homeless, and the station was dark and desolate, making me feel a bit uneasy from the start. The decisive reason we stopped using the CTA afterward was the moment when the train lost power, and all the lights went out, causing the train to stop. Fortunately, it started again after 2-3 minutes, but I worried about what would happen if such a situation occurred again, so we opted for Uber afterward.
During our trip, we stayed at the Trump Hotel. Since we did not rent a car, we looked for a convenient place to stay and chose this hotel located in the heart of Riverwalk. Ultimately, the choice of location was excellent. The Chicago River flows right in front of the hotel, providing an impressive view from the window, and major tourist attractions were within walking distance, making it very convenient to get around. The room was spacious and tidy, and the bathroom was clean and well-maintained.
Additionally, being able to enjoy breakfast for two and a $100 credit benefit through the American Express card was a significant advantage. Thanks to this, we didn’t have to search for a restaurant separately and could leisurely enjoy breakfast through room service. There were various options on the breakfast menu, and all the dishes we ordered were satisfying in both taste and quality. While the hotel’s location and service were excellent, I believe these thoughtful benefits contributed to a higher overall satisfaction.
Trump International Hotel & Tower® Chicago
Chicago is often called the ‘Windy City’ due to its strong winds and is also famous for its unpredictable weather. Fortunately, when we traveled there, the weather was really nice. The sunshine was warm, and it felt slightly hot while walking, but once we stepped into the shade, a cool breeze made it quite pleasant. Overall, it felt similar to the weather in LA, making it perfect for wandering around all day. Although the temperature dropped slightly in the evening, a light jacket was sufficient, so we didn’t have to worry much about our outfits throughout the trip.
Millennium Park, Cloud Gate, The Art Institute of Chicago
The first place we visited was Millennium Park. It took about 12 minutes to walk from the hotel, and we arrived quickly while strolling along the riverwalk and checking out downtown streets. As we walked a bit inside the park, we came across a bustling area filled with people, which is where Cloud Gate is located. This sculpture, commonly known as ‘The Bean,’ was much larger and more overwhelming in person than I had imagined from photos. Its mirror-like surface reflected the surrounding scenery and people, making it fun to look at.
After checking out The Bean, I took a leisurely stroll through Millennium Park and headed to The Art Institute of Chicago. I arrived around 11:05 AM, just before the museum opened, and there was already quite a long line of people waiting to get in. I had purchased my ticket online in advance, so I could enter right away, but the line for on-site purchases was longer than I expected. If you want to avoid waiting in line, I definitely recommend booking your tickets online in advance.
Inside the museum, there were truly a variety of exhibitions, and I was particularly looking forward to the Van Gogh exhibition. However, it seemed that many others had the same idea, as the exhibition hall was quite crowded. At first, I tried to move along the line to get a closer look, but it took too long, so I eventually decided to enjoy it from the back. The museum is quite large and has diverse exhibitions, so it’s best to allocate enough time for a leisurely visit. There are also spaces inside where you can enjoy meals or coffee, so if you plan to stay for a long time, taking a break here might be a good choice.
The Art Institute of Chicago
Skydeck
After exploring the museum, I headed to the Skydeck, which I had reserved in advance. It was about a 15-minute walk from the museum to the Skydeck, and since I passed through downtown, it was perfect for enjoying the cityscape and taking photos while walking slowly. Fortunately, the day we visited was Memorial Day, so there were events happening all over the streets, adding unexpected joy to our experience.
When I arrived at the Skydeck, the path to the elevator was decorated with a Chicago theme, allowing for sightseeing and photo opportunities along the way. This area, designed like an exhibition space, felt more like an experience than just a waiting time. Once I took the elevator up to the observation deck, there was a glass-floored photo zone where you could line up to take pictures in turn. There were about four glass photo zones, and each team entered one at a time to take photos. According to the website, if there are three or fewer people, you get 60 seconds, and if there are four or more, you get 90 seconds. Because of this, the line was quite long, but it moved quickly, so I didn’t have to wait too long. Once on the glass floor, a camera installed on the ceiling automatically took a picture first, and after that, each team had 60 seconds to pose freely for photos. Standing in front of the glass floor made my legs tremble, and while I wondered if it was really that scary when I saw others being afraid, once I got up there, it was much scarier than I expected.
After finishing the experience, if you go down, you’ll find a souvenir shop where you can check and purchase the photos you just took. The price varies depending on how many photos you choose, and I bought them all, which I remember costing about $55. For your reference, you can only download the photos online if you actually purchase them, and while the price is somewhat high, I decided to buy them as they would serve as a nice memory.
Skydeck Chicago
Wendella Tours & Cruises
One of the things I highly recommend when visiting Chicago is the architectural tour enjoyed from the Riverwalk. The skyline of Chicago viewed from the river has a different charm compared to seeing it from the city center, and I was able to look at the city in a unique way while listening to the stories behind each building. I booked with Wendella Tour, but the prices and durations vary slightly depending on the tour company or type of tour, so I recommend visiting their website to compare prices and schedules before making a reservation.
We booked a 90-minute architectural tour that departed at 6 PM and returned around 7:30 PM. I recommend arriving 30 minutes before the tour starts; I arrived about 15 minutes early and found quite a few people already waiting in front. If you have a reservation, there shouldn’t be any issues boarding, but arriving too late might make it difficult to get a good spot. Once the tour starts, the guide provides detailed explanations about Chicago’s major architectural landmarks, and it was nice to leisurely appreciate buildings that are hard to see or easy to miss when walking. As we moved along the river while listening to the explanations, I was able to view Chicago’s architectural beauty from a different perspective, and it was an optimal environment for taking photos, making it a must-try experience during your trip.
Wendella Tours & Cruises
360 CHICAGO
After finishing the cruise tour, I headed straight to 360 Chicago. It took about a 15-minute walk from the cruise boarding location, and it was the time when the city’s night view began to light up, making the walk quite atmospheric. Even though I had already visited Skydeck during the day, I returned to 360 Chicago specifically to see the night view of Chicago. Both observation decks have their own charm, but since the views and times differ, I was able to enjoy Chicago in a different way.
We had a reservation for 360 Chicago at 8:30, but we had to wait longer than expected. It seemed like the crowds were due to it being Memorial Day. We were quite exhausted from walking around the city all day, and the long wait was a bit tough, but the moment we reached the observation deck and faced the Chicago skyline at night, the wait felt worth it. 360 Chicago has an experience called ‘Tilt,’ where the glass window slowly tilts outward, allowing you to look down. I thought it would be too scary to try, but for those looking for a unique thrill, it might be worth a shot. The Tilt experience has a separate fee, so if you’re interested, I recommend checking the official website for more details.
360 Chicago
Andy’s Jazz Club & Restaurant
The last stop of the first day was Andy’s Jazz Club. I had always wanted to visit a jazz bar, and having that first experience in Chicago felt even more special and exciting. When we arrived, there was already a line of people waiting to get in, and entry was allowed about 15 minutes before the show started. The music coming from outside and the atmosphere inside heightened our anticipation.
Since we had reserved a Main Seating Area / Table, we were lucky enough to be seated right in front of the stage. At first, I worried it might be too close, but it actually allowed me to focus more on the performance, which I was very satisfied with. For dinner, we ordered shrimp risotto, nachos & guacamole, along with beer and cocktails, and the food was even better than I expected. Enjoying a beer alongside live jazz made me feel the travel fatigue accumulated throughout the day melt away. The performance was immersive, and the hour passed by in an instant. It was a bit disappointing when it ended, but the encore song they played at the end was a perfect conclusion.
Andy’s Jazz Club & Restaurant
Riverwalk
On the morning of the second day, we decided to take a leisurely walk along the Riverwalk, which we had passed by during the cruise on the first day. After exiting the Trump Hotel, it took only about three minutes to see the Riverwalk bridge, and there are stairs that lead down below. Walking along the river, there are stairs that go up and down at intervals, allowing us to stroll freely between the upper city streets and the lower Riverwalk. Since it was morning, it was quiet, and a cool breeze made it a perfect time for a pleasant walk.
I didn’t realize it while on the cruise, but there were quite a few places to explore inside the Riverwalk, including restaurants, cafes, and souvenir shops. It was fun to go inside the stores and watch people kayaking on the river. The weather was so nice that my pace slowed down, and I ended up enjoying the Riverwalk leisurely for quite a while. I would recommend it as a walking route to experience downtown Chicago from a different angle.
Navy Pier / Garrett Popcorn
As I walked along the Riverwalk, I naturally moved towards Navy Pier. I stopped by the Chicago Children’s Museum on the way, and I was surprised to find that it had many restaurants and stores inside, contrary to my initial impression that it was just a simple exhibition space. I took a break and had coffee at Starbucks, and right next door was the famous Garrett Popcorn shop in Chicago, so I naturally stopped by to grab a snack.
I ordered the smallest size of the Garrett Mix to try, but it didn’t quite suit my taste, perhaps because I had high expectations. My brother said it wasn’t good either. If you’re like me and might not enjoy it, I think it’s best to start with a small size to taste and decide. After eating the popcorn, I went back outside and sat on a bench in front of Navy Pier, resting for quite a while. There were many people around us enjoying the leisurely atmosphere, and with the gentle breeze and coffee in hand, it was hard to get up. As the time to return to LA approached, I felt a stronger sense of regret and a desire to stay longer.
Lou Malnati’s Pizzeria
In Chicago, Giordano’s, Uno, and Lou Malnati’s are considered the three famous pizzerias known for deep-dish pizza. After looking through several reviews, I decided to go to Lou Malnati’s, as it seemed like it would be the tastiest. I arrived around 2:30 PM, and there were quite a few customers inside, so I was told I would have to wait about 15 minutes. However, when I asked if there were tables available outside, the staff checked and guided me to a seat right away, so I was able to sit down faster than expected.
After returning to the hotel and finishing unpacking, I had pizza and pasta, and the pizza was absolutely delicious. I thought it might have lost some flavor after cooling down, but I didn’t expect it to be this good. I couldn’t help but wonder how much better it would have been if I had eaten it right when it came out. The dough was particularly impressive, and my brother said, “If we had eaten it at the restaurant, we would have ordered another one,” expressing his regret. On the other hand, the pasta was really disappointing compared to my expectations. I heard that Lou Malnati’s salad is also quite famous, so if I come back next time, I definitely want to have the pizza again and try the salad instead of the pasta.
Lou Malnati’s Pizzeria
A fulfilling 2-night, 3-day trip from LA to Chicago. Although short, every moment spent eating, seeing, and feeling will likely stay in my memory for a long time. It was a much more charming city than I expected, and if I get the chance to visit again someday, I would like to fill in the gaps of what I missed this time. For those planning a trip to Chicago, I hope this review serves as a small help.
