Three Days in Chicago – Our Experience

Over the Memorial Day weekend, we traveled for the first time to Chicago, IL to discover all that this big city had to offer. Our trip was an awesome experience and if you have been thinking about visiting, we are here to give you an idea of what its like and things to do.

Day 1:

After checking into our hotel which was conveniently located downtown on the Michigan Avenue strip, we immediately set out to discover our surroundings. Our first stop was to the acclaimed Art Institute of Chicago. After reading several reviews that mentioned this place as a must visit, we decided to explore it for ourselves. The museum was massive and included a great collection of artifacts, portraits and sculpture displays from all parts of the world. All of the items were very stimulating to the eyes, and it was just awe-inspiring to see the handwork of so many great artists. We were only disappointed that the museum did not seem to contain a lot of African-American art as we always like to see the contributions of our heritage in these types of places as well.

After leaving the Art Institute, we walked our way to the Willis Tower, formerly known as the Sears Tower, so that we could view the city from what used to be the tallest building in the United States [its now the 2nd tallest]. Unfortunately, the wait period to get to the observation deck of the Willis Tower was about two hours, so we decided to skip this activity. We used the extra time to walk around the area to explore more of the city. Along the way, we came across some recognizable buildings such as the Chicago Theater and the the Trump Tower.

Later in the afternoon, we caught a Lyft to Millennium Park to check out the Chicago House Music Festival. We had never heard this type of music before but it was dance worthy and the locals were very much into it. While in Millennium Park, we also couldn’t miss the opportunity to see the popular Cloud Gate sculpture which is a major attraction in Chicago. We loved how it reflected everyone’s image and the skyscrapers surrounding it.

Making our way from Millennium Park, we took some time to scroll along the shore of Lake Michigan and to gaze out at how enormous this body of water seemed. The greenery of the lake makes for a beautiful sight.

Across from the lake where we were is the great Buckingham Fountain. This fountain is huge and the water shoots up way high. On a very hot day in Chicago, the mist from the fountain is very welcoming. We were lucky enough to come upon the fountain just as it was turning dawn. Since the fountain lights up with many colors at night, it became a dazzling centerpiece. The views of the city from this area was also spectacular.

With all of the exploring we did in Chicago during the day, of course our belly’s were craving a Chicagoan style meal for dinner. What better way to end our first day than with deep-dish pizza. We stumbled upon Lou Malnati’s Pizzeria who boast that they are home of the best deep-dish in Chicago. Everyone must have gotten that memo because the place was bananas and the seating time was more than what we were willing to wait. Nonetheless, we ordered our pizzas to-go, then enjoyed them back at the hotel. We’ll just say that the deep dish pizza was good, but it wasn’t the best we’ve ever had.

Day 2:

Our second day in Chicago started with breakfast at the popular Wildberry Pancakes and Cafe. The food was good and the portions were plentiful. We also found out that our server was in the process of moving just up the street from us in Myrtle Beach, SC – small world!

After the hearty breakfast, we decided to grab another opportunity of viewing the city from an observation deck. Since we were right near Chicago 360, we gave that one a chance. This time we made it to the top in very little time. We were able to view the city from all sides while on the 94th floor of the John Hancock building. After leaving Chicago 360, we went shopping down Michigan Avenue checking out all the high-end retail stores, but making sure to keep our wallets closed for the most part.

In the afternoon, we traveled to the Southside of Chicago to visit the DuSable Museum of African-American History. Although the museum was not as impressive as we had hoped, we did learn a lot about Harold Washington, the first Black mayor of Chicago. There were also some relics from the slavery era including the front page of an 1804 Charleston Courier newspaper which list the sale of slaves in Charleston, SC. We did wish that there were more to see inside the Museum, but we saw that they have plans to expand the facility. After leaving the museum located in Hyde Park we did waver with the idea of walking the distance to see the Obama’s Chicago home since it was also in the vicinity. However, we decided against it since the street where their house is located is blocked off to public foot traffic.

Once we left the museum, we rode back to the downtown area to walk around Navy Pier. There were lots of people there. We did not stay too long but it was nice to scroll through, see the Centennial Wheel, and people watch.

We were able to complete a full day of activities all in time to check into our dinner reservation at Joe’s Seafood, Prime Steak & Stone Crab. There are only three locations of this restaurant in the U.S., and we will say that the seafood at the Chicago location was delectable! The restaurant is a bit pricey, but we also enjoyed the fine dining experience and the seafood mustard sauce!

Day 3:

On our last full day being in the city, we started it off with taking a riverboat architectural tour cruise. This cruise was very interesting as we learned about the history behind the styles and structure of the beautiful skyscraper buildings.

Being on the river offered an alternative view of the city which we enjoyed, but the tour lasted long enough to make us hungry for a good meal. Having studied the transportation system prior to our trip, we hopped on the “L” and rode it north of the city to the Lincoln Park neighborhood where we had brunch at the famous Black-owned restaurant, Batter & Berries. This restaurant is known for their flavorful french toast among other things, so naturally french toast is what we opt to have. The dish did not disappoint! And the butter served with the meal was a sweet bonus. This place was also very busy, but lucky for us we did not have to wait long for a table.

Just as we were finishing our meal, it began to pour outside. We were hoping that the prediction of rain would be inaccurate especially since the morning started off so nice, but the rain did ruin our plans to go to the Lincoln Park Zoo after brunch. Instead, we called a Lyft to transport us back to the hotel. Our bodies must have been tired from all of the walking and sightseeing because in no time we were all fast asleep, napping away the remainder of the afternoon. When we woke it was still raining, but once the rain had subsided, we decided to go out and do some window shopping along Michigan Avenue’s Magnificent Mile. On this evening we did not stay out too long as we had to get ourselves ready for our departure, however we made sure not to leave the city without having a Chicago style hot dog especially since it was Memorial Day.

In three days, we got to explore a lot in Chicago from downtown, to the North, and the South sides. We are actually proud that we got to do most of the activities on our itinerary. Our favorite part of the trip was the spectacular views of the city’s skyline. We were also impressed by how clean the downtown area appeared to be. Of course we came across homelessness and people doing crazy things like dancing in the street in the way of oncoming traffic, but we are grateful to have remained safe the entire time.

Chicago is definitely a city we would recommend visiting especially when the weather is warm. On our trip, the weather did fluctuate, but we were dressed appropriately at all times. The city is so vibrant with festivals, events, restaurants and shopping, there is always something to do. We hope to return to the Windy City someday soon but for now we will cherish our memories of the three days spent in Chicago.

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