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City Colleges of Chicago first opened its doors on September 11, 1911 as Crane Junior College. Nicknamed "the people's college," it was established under the Chicago Board of Education as a way to provide high quality, affordable education accessible to all in Chicago. There were just 30 students in the first class.                   

By 1929, Crane Junior College, with 4,000 students, was the largest junior college in the country. But, the college was forced to close in 1933 during the Great Depression. There was an immediate public outcry, led by students, faculty, members of Chicago's growing labor movement, and most notably, attorney Clarence Darrow. The college reopened less than a year later as Herzl Junior College. Two new sites were added: Wright Junior College on the Northwest Side, and Wilson Junior College on the South Side.                   

During World War II, the colleges were taken over by the military for use as training facilities. After the war, soldiers returning to school on the GI Bill filled City Colleges to capacity.                   

In the 1950s, Truman College opened as an evening college at Amundsen High School. Fenger College and Southeast College also opened consolidating to create Olive-Harvey College two decades later.           

Expansion continued in the 1950s, with the opening of Bogan Junior College on the Southwest Side (later renamed Daley College) and Loop College Downtown (later renamed Harold Washington College). In 1968, students closed down several City College campuses amid civil rights issues. To recognize the key civil rights leaders, Herzl College was renamed Malcolm X College and Wilson College became Kennedy-King College.           

WYCC TV began televised instruction in the 1980s through the Center for Distance Learning and Olive-Harvey College's South Chicago Learning Center opened.                   

Satellite sites continued to grow as well. Humboldt Park Vocational Education Center and Arturo Velasquez West Side Technical Institute opened in the 1990s under Wright and Daley Colleges respectively and Dawson Technical Institute became part of Kennedy-King College.          

In 2007, a brand new Kennedy-King College opened at 63rd and Halsted Street which houses WYCC TV, Washburne Culinary Institute, and WKKC Radio.           

As City Colleges approached its 100th anniversary, Chancellor Hyman launched the Reinvention initiative in 2010. The centerpiece of the Reinvention effort is to ensure student success, drive greater degree attainment, job placement and career advancement and become the economic engine for the city of Chicago. The initiative is a long-term, ongoing effort designed to ensure CCC continues to benefit Chicago into its second century.​​​​​​​​​​​​​​​

In order to prepare Chicagoans for careers in growing industries, City Colleges launched the College to Careers initiative in 2011. The initiative partners City Colleges faculty and staff with employers and universities in fast-growing industry sectors to help align City Colleges curricula and facilities so students are prepared with skills to succeed in the workforce. These partnerships also provide City Colleges’ students access to real-world experience via teacher-practitioners, internships and first-pass at job opportunities. 

To help eliminate the barrier of cost and allow students across Chicago to achieve the dream of attending college, Chancellor Hyman partnered with Mayor Rahm Emanuel to introduce the Chicago Star Scholarship in 2014. The scholarship guarantees completion-ready students with a 3.0 GPA at Chicago Public Schools, starting with 2015 graduates, a free education for up to three years at City Colleges of Chicago, after the application of financial aid. In its first semester, the Chicago Star Scholarship helped nearly 1,000 Chicago students go to college for free. Following the introduction of the Star Scholarship, City Colleges entered into partnership agreements with many four-year colleges and universities across Chicago to offer further financial incentives to students planning to transfer after completing at City Colleges.​​