After waking up and grabbing breakfast at the hotel, everyone met in the lobby around 9:00 AM to start the day. We hopped onto a bus for a guided tour of Chicago led by Shermann “Dilla” Thomas. He brought so much energy and storytelling to the tour that it felt less like a typical bus ride and more like hearing the city’s history from someone who truly loves Chicago.
As we drove through different neighborhoods, Dilla pointed out places that hold important stories in the city’s past. One powerful moment was passing the former home of Emmett Till, whose story became a major catalyst for the Civil Rights Movement. Seeing the neighborhood while hearing the story made the history feel especially real.
We also drove past areas connected to legendary figures like Muhammad Ali, and the area known as O-Block, which Dilla explained in the context of Chicago’s culture and music scene.
Another highlight was passing the site of the future Obama Presidential Center, the library and museum being built for Barack Obama. We also heard the fun story about where Michelle Obama and Barack had their first date, which happened at a Baskin-Robbins that has since become a Subway.
After the bus tour, we stopped at Strugglebeard Bakery, which quickly became a highlight of the morning. As soon as we walked in, the smell of fresh baked pastries filled the space.
We got to try several samples of sweet treats, which made it fun because everyone could taste a little bit of everything. Many people also ordered their own snacks, the brownies and hot chocolate were especially popular and quickly became favorites in the group.
Visiting the National Museum of Mexican Art was a really cool experience. The museum had a wide range of artwork that showed different parts of Mexican culture and history. There were colorful paintings, detailed sculptures, and intricate beaded pieces, and each section had its own style and story behind it. Walking through the galleries, it was interesting to see how the art reflected traditions, identity, and important moments in Mexican and Mexican-American communities. Overall, it was a fun and eye-opening stop that gave us a chance to see a lot of creativity and culture all in one place.
We then went to Taqueria Los Comales for lunch, where everyone enjoyed some authentic Mexican food. Afterward, we took the Chicago 'L' back downtown and returned to the hotel for some downtime
Our next adventure began with a walk to Navy Pier, this is where we did FlyOver. A “roller coaster” that takes you over Chicago. We then had some time to walk around, shop, and choose our own dinners.
This attraction is a motion ride that makes you feel like you are soaring over the city, giving us incredible aerial views of Chicago’s landmarks.
Once our time at Navy Pier wrapped up, we walked over to The Great Escape Room Chicago. We split into two groups: one group attempted the Surgical-themed room, while the other tried the Midnight Heist challenge. In the end, the Midnight Heist team wasn’t able to finish in time. Meanwhile, the Surgical team decided to have some fun by sneakily crawling through one of the escape room pathways and surprising the other group, which definitely caused a few good scares.
The night ended with lots of laughter, but also a bit of a rush as we hurried back to the hotel in the pouring rain. Even though we got a little wet, it was a memorable way to wrap up a full and exciting second day in Chicago.