In 2005, the group went to Chicago, Illinois, to explore new cultures and backgrounds. Fundraising efforts yielded $50,000 to cover trip expenses.

During the trip, Diversity Project students had the opportunity to interact with students from Manuel Perez Jr. Elementary School, located in the Pilsen neighborhood of Chicago, home to the largest Latino community in the Midwest. Differences were highlighted and explored, and similarities discovered and celebrated. Students from Perez visited McLean County a few months later.

The trip began with a visit to the Holocaust Memorial Foundation of Illinois, and students heard from a Holocaust survivor who escaped at age six. A visit to the International Center on Deafness and the Arts in Northbrook exposed the group to a world without sound. Other activities included a visit to Chinatown, the Mexican Fine Arts Center Museum, the DuSable Museum of African American History, and the Indo-American Center. The group also had training at the City of Chicago's Commission on Human Relations.