Two Windy Days in Chicago


Right before the COVID outbreak in the US, I went on a work trip to Chicago and left just a few days before the 14-day mandatory quarantine in Taiwan. The average 13.5h flights were perhaps the most restless ones I’d taken, wearing a mask all the way and skipping meals if possible. Despite the stress from COVID, I am still glad I got to explore Chicago for a bit after my last visit ten years ago as a graduate student.


Architecture boat tour

Luckily, it was a sunny day when I went on the 90-minute river tour with Wendella. Originally, I was looking at the tour by Chicago Architecture Center but their river tour is seasonal from late May to October. Later I found Wendella, which also ran the water taxi during commute hours and I had a great time exploring the city architecture along the river from Michigan Lake down to the Chinatown. I enjoyed learning about the history and stories of the city itself and many buildings from our local guide. My favorite building complex was perhaps Marina City, with two 65-story round towers that stood out at night.

Architecture boat tour, Chicago State Street, Chicago (Day)

Skydeck at Willis tower

Willis Tower (formerly Sears Tower) is probably one of the most iconic buildings in Chicago, that used to be the tallest building in the US. I would strongly recommend coming here at a quieter time, as I waited about 3 hours on a Monday around 12:30 pm while spending less than 10 minutes on the Skydeck. The view of the city from different angles was amazing. There was a rail to the glass windows, and it was not so easy to take photos with a camera. I liked the ledge experience, a glass platform extending out from the building at 1353 feet up that certainly gave me a quick thrill.

Skydeck at Willis tower, Chicago Skydeck at Willis tower, Chicago

Millennium Park

Given sunny and warm weather, I could spend hours at this beautiful park in the middle of the city. When I first visited the city in snowy wintertime a few years ago, I only visited the Cloud Gate, aka the bean, for five minutes. This time, the weather was relatively warmer and I spent about half an hour walking through the park. There were creative decorations along the way, like the fountains with an ever-changing face (Crown Fountain).

Millennium Park, Chicago Millennium Park, Chicago

The Art Institute of Chicago

I was pleasantly surprised by the amount of art this museum housed and enjoyed every corner of it during my 3-hour visit until my energy was exhausted from walking. As a fan of the Impressionist style paintings, I got to see so many fine paintings from the artists I admired and listened to their stories with the audio guide. There were also quite a few contemporary exhibitions with modern media that complemented the rooms of paintings.

The Art Institute of Chicago The Art Institute of Chicago

Chicago Cultural Center

The cultural center is right across from Millennium Park, and I spent about 1.5 hours walking through two exhibitions: A Retrospective of Cuban Printmaker Belkis AyĆ³n and In Flux: Chicago Artists and Immigration. Perhaps the winter season was a bit quiet, these were the only exhibitions in this big building at the time.

Chicago Cultural Center Chicago Cultural Center

Food highlights

Deep dish pizza at Lou Malnati’s Pizzeria

Ten years ago, I tried Chicago’s famous deep-dish for the first time at Giordano’s. This time, I only got to have deep dish pizza once at Lou Malnati’s that was strongly recommended by coworkers who were locals. I loved that they offered personal size pizza, and I finished the whole pie quickly. The tomato was very fresh and the butter crust was my favorite part.

Deep dish pizza at Lou Malnati's Pizzeria, Chicago

Chicago style hot dog at Portillo’s

A few years back I first had the Chicago style hot dog from Gold Coast Dogs at the Midway airport, and I really liked the combination. The neon green pickle relish scared me at first sight (it was from a blue dye), but it was also very unique. Portillo’s had a Western-themed interior, and there were many tables for a quick bite. Other than hot dogs, they also had other items like burgers and fries.

Chicago style hot dog at Portillo's, Chicago


I particularly enjoyed my stay at the River Hotel, a Club Quarters hotel along the Chicago River. It was just a few minute’s walk from multiple metro stations, and walking distance to the Millenium Park area and a bunch of shops within few blocks. Since I was in Chicago for a week, it was also helpful having complimentary self-service laundry in the hotel. The room was spacious and affordable, I’d certainly recommend staying here.


Despite the chilly weather this trip, it was still sunny and warm enough at times to take a long walk outside. Chicago was a fun city for watching a show/concert/ball game, and I could find almost all the shops that I used to go within walking distance from downtown. I didn’t get to explore too much outside of the loop this time, and I would love to check out other neighborhoods next time.

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