In 1999, the then President Hugo Sonnenschein announced the relaxation of the university’s famous core courses, reducing the number of required courses from 21 to 15. When the New York Times, The Economist and other major news media picked up this story, the university became a national education debate focus. These changes were eventually implemented, but the controversy played a role in Sonnenschein's decision to resign in 2000.
Starting in the mid-2000s, the university began a multi-million dollar expansion project. In 2008, the University of Chicago announced plans to establish Milton Friedman College, which attracted support and controversy from faculty, staff and students. The institute will cost approximately $200 million and occupy the buildings of the Chicago Theological Seminary. In the same year, investor David G. Booth donated US$300 million to the University’s Booth School of Business. This is the largest gift in the history of the university and the largest gift ever made by the business school. In 2009, several new buildings are under planning or construction, half of which cost US$100 million or more. Since 2011, major construction projects include Jules and Gwen Knapp Biomedical Discovery Center, ten floors Gao's Medical Research Center and the further expansion of the University of Chicago Medical Center Medical Park. In 2014, the university launched a public fundraising campaign that raised $4.5 billion. In September 2015, the university received $100 million from the Pearson Family Foundation for the establishment of the Pearson Institute for Global Research and Resolution and the Pearson Global Forum at the Harris School of Public Policy Research.
On May 1, 2014, the University of Chicago was named "one of the 55 higher education institutions under investigation" by the Office of Civil Rights, "because the White House mission may violate federal laws to handle complaints of sexual violence and harassment" to protect students from sexual assault power.
In 2019, the university created the first school in thirty years, the Pritzker School of Molecular Engineering.