3 Day Chicago Itinerary

Chicago, a city surrounded by a giant lake, has the most gorgeous architecture and the greatest pizza that you've ever tried. Chicago will always have a piece of my heart, and it's easier to see why the city captures so many who visit!

Before you start planning, I would highly recommend purchasing the Chicago City Pass. If you want to go to at least 3 of these attractions, it makes the most sense to purchase this pass, as it saves you money.

Day 1: Architecture, Astrology, and Animals Glore

On our first full day in Chicago, we had to try the Michelin-starred Filipino restaurant called Kasama. This place does not take reservations during the day and is crowded. We went right when it opened, and there was already a massive line. They have cool Filipino-inspired drinks and pastries. We went a little overboard in ordering, but it was definitely one of my favorite places to eat in Chicago.

After breakfast, we went over to the famous Shore Sightseeing Architecture cruise. The cruise did not disappoint. We learned about the different periods of architecture, from Art Deco (represented by the Merchandise Mart and the Opera building) to modernism. Some of my favorite buildings to see were the Chicago Tribune and St Regis. It is a great way to experience the skyscrapers in Chicago in a small period of time.

Afterwards, we headed over to Lincoln Park. Lincoln Park is a giant park that has the zoo, the Chicago History Museum, and the conservatory. It is a great place to walk around and explore the city's green spaces. The zoo has a great African journey exhibit where the weather mimics the weather in Africa. A hidden gem inside the zoo is the Honeycomb. The honeycomb is a honeycomb-like structure, where it is almost like an architectural inception, where you can see architecture inside of architecture (e.g., skyscrapers inside the honeycomb). It is great for a photo op! When you are near Lincoln Park, you can walk to see the mansions in the neighborhood, including Theurer-Wingley House.

To end our day, we headed over to the Adler Planetarium. This is a unique attraction where you can learn about the history of astrology as well as witness the simulations. We saw a show on the Tour of the Solar System where we got to see what the clouds of Iota (Jupiter's moon) would look like.

Day 2: An Exploration of Skydecks, Aquariums, and Paintings

On our 2nd day, we headed over to Millennium Park to view the most iconic sculpture, Cloud Gate, also known as the bean. Cloud Gate is a public sculpture by the artist Anish Kapoor. This sculpture now has lights underneath it and is truly one of kind. It is so cool see all the different ways that people take pictures with the bean. Unfortunately, I will have to venture back to get my perfect picture, as it was under construction, but you definitely should not miss it on your trip to Chicago!

Inside Millennium Park, you can also view the Jay Pritzker Pavilion, Lurie Garden, and the Crown Fountain. The Jay Pritzker Pavilion is a cool amphitheater where they host a lot of local concerts. It can host about 11,000 people! When we were there, there was a national choir competition happening. Lurie Garden is also known as the secret garden and is a great place to relax and experience the green spaces. The Crown Fountain is interesting as it is a fountain with a bunch of different faces of people from Chicago as the fountain spits out water. It is quirky and fun!

After exploring Millennium Park, we headed over to the one and only Art Institute of Chicago. If I were you, I would recommend going immediately when they open and planning exactly where you are going first. For me, I'm a huge fan of impressionism, and I went straight to my favorite painting, On the Sunday at La Jatte. This place can become Disneyland rather quickly, so I would try to come as early as possible to avoid crowds.

Once we finished exploring the art museum for a couple of hours, we headed over to the Shedd Aquarium. The Shedd Aquarium is a massive aquarium inside a neoclassical temple. When you first arrive, you can start by petting the starfish. One of the most impressive things about this aquarium is the Wild Reef, located on the bottom floors of this building, where you can view all different kinds of sharks and even a chocolate chip sea star. There are also many different experiences that you can purchase to get to know the creatures of the sea better.

After exploring the aquarium, we got some Chicago-style pizza at the one and only Giordano's. I know it's a chain, but it is a good chain for a reason! One thing to remember is that Chicago pizzas can take over an hour to cook, so make sure that you have enough time to wait and then eat your pizza!

Once we finished eating, we headed over to the iconic Skydeck of Chicago. Now, I will preface that there are two different sky decks in Chicago. There is 360 Chicago and another one called the Skydeck of Chicago. After doing my research, I really liked the Skydeck of Chicago because it is the original skydeck where you can see 4 states all at once. It is also higher than 360 Chicago. However, you can check out the differences here.

If you choose the Skydeck, you get about 30 seconds to take a picture after getting in line. I wouldn't stress too much, because you are able to re-enter the line if you don't like the ones that you originally took. We decided to book our tickets 30 mins before sunset, and we are so glad that we did! This way, we are already there before sunset and can get our golden hour pictures!

Day 3: Exploring Chinatown

On our very last day in Chicago, we decided to venture out into the Chinatown neighborhood. If you are staying anywhere near the water taxis, I encourage you to try the water taxis out and to take them out to Chinatown. It is really neat and unique to be able to take a water taxi from one part of the city to the next.

Once we arrived in Chinatown, we decided to start with getting dim sum at Ming Hin Dimsum. Dim sum is one of my favorite foods to have for breakfast/brunch. After we finished eating, we went over to Ping Tom Park. The park has four pillars, train tracks, a large Chinese architectural structure, and a playground. The park is named after Ping Tom, who was an influential Chinese businessman who was essential in developing the community within Chinatown.

Afterwards, we decided to venture to the Chinese American Museum. The museum is free. It covers a lot about the Chinese diaspora in the US and is the only museum of its kind in the Midwest. It was disheartening to learn about the racism that the Chinese people endured, which led to the Chinese Exclusion Act in 1882. It was also interesting to hear the stories of Chinese soldiers and learn that they have been a part of wars since the Civil War in the US.

Once we finished with the museum, we headed over to Tanta Cocina Peruana for some delicious Peruvian food. This restaurant has a great vibe with an excellent rooftop to enjoy views of the city.