As we were getting ready to visit our family in the US two years ago we decided to book our flights via Chicago to do a two-night layover on our way from Bangkok to Florida. I had never been to Chicago and I was overly excited to visit this city for the first time ever.

Evan was about 7 months old at the time and crawling all over the place.  We rode the metro to the main train station in the city center and it wasn’t bad at all, despite our suitcases and stroller. After arriving in our hotel located in the Magnificent Mile all we could think of was how great it was to be in America, be able to ride on excellent public transportation and actually walk on the sidewalks (vs. avoiding huge gaps or food stalls).

We stayed at the Hotel Cass by Holiday Inn Express. The room was small but nice and clean and we had a nice view of the magnificent mile. I don’t remember how much it was, but I recall it was a good deal for the location and the season.

The first day we slept all day, we were overly tired from jet-lag and traveling with a baby. We only visited the Navy Pier and walked all around it. Evan got really scared of the birds flying by. I then realized he had never seen a bird before although he had ridden on an Elephant and petted a baby tiger. The Navy Pier is so fun. There are some carnival rides, food stands (yay for Ben and Jerry’s!), a theater that was playing the Shrek Musical at the time, and lots of opportunities to ride on tour boats. They have some nice restaurants and a few shops and it’s a great place to enjoy the ocean breeze and stroll by.

Of course being in Chicago we had to try the famous deep-dish pizzas. We were eager to eat some real American fare. We visited UNO Chicago Grill at its Pizzeria Uno location to finally take a bite of the legendary dish. It did not disappoint but it was just too much to handle for our stomachs now used to rice and more rice as its main source of nutrition. We were able to eat about half of it and they offered a take-away bag. We declined as we were already devising dinning plans for our second day in Chicago.

Second day there, we slept in again and decided to check out some of the shops in the Magnificent Mile. After being “deprived” of (affordable) American brands in Bangkok the sales in many of the stores lifted my spirit. We didn’t want to shop much since these were our first days in the US but we scored a few baby gap outfits for Evan at rock-bottom sale prices.

After (window) shopping until the baby dropped we strolled to the Millennium Park. We had lunch at a lovely brasserie and then headed to explore the park. It was so nice so see a park so clean and inviting. After checking out some amazing sculptures we headed to the famous Bean. We spent at least an hour there taking photos of Evan making faces and staring at his reflection. It was then that I realized that kids (even infants) really  benefit from exploring new places. Evan had a blast and simply loved this experience.

On our last evening in Chicago we wined “beered” and dined at Portillos restaurant. This place is famous for its hotdogs and they did a great job of quenching our American beer cravings and giving us a taste of the all-American beef hotdog.

Our short trip to Chicago came to an end way too fast. The next morning we woke up had a quick breakfast at the Hotel and headed to the airport.  We left Chicago staring out a rainy taxi window and vowed to come back and explore every last bit of it.

Chicago and Evan Sights

Disclaimer: It’s more Evan than Chicago, and mostly at The Bean in Millennium Park.