[8] The district encompasses nearly 11.5 square miles (30 km2) drawing students from Homewood, Flossmoor, Chicago Heights, Glenwood, Hazel Crest, and Olympia Fields.

[9] A three-time U.S. Department of Education Blue Ribbon Award Winner (1983, 1996, 2002),[10] Homewood-Flossmoor continues to be ranked nationally, including as one of America’s Best High Schools by U.S. News & World Report in 2020.

As growth continued, it became apparent that a major new facility was needed, and in 1971, the North Building and fieldhouse opened when the student population topped 4,000.

Following a decade of preparation and fiscal planning, in 1995 a $25 million renovation and addition program was completed: all classrooms and offices were wired for internet access; a music wing was added, providing student practice and performance; a Technology Center and numerous labs to offer computer assisted instruction were completed; the Mall Building, located mid-campus near the football field and field house, was expanded, modernized and staffed, providing athletic training and rehabilitation of student athletes; a new Olympic sized aqua-center was opened; 14 tennis courts were added; and the student-run WHFH radio and TV stations were modernized.

In 1989, football coach John Wrenn proposed District 233 adopt a mandatory drug-testing policy similar to one at two Lafayette, Indiana high schools, where a recent landmark court case decision allowed the creation of such programs.

[15] H-F became the first high school in Illinois to require mandatory random drug testing for its student athletes.

In 1996, up to 20,000 people gathered on the school lawn to hear President Bill Clinton deliver a speech on education during his 1996 reelection campaign.

H-F now joins the exclusive company of approximately 3,000 IB World Schools that dot the globe across 138 countries.

Jesse Jackson led an assembly at the school to address a blackface incident that prompted a student walkout.

[citation needed] In 1990 there was a proposal that would allow a student to substitute an academic class in place of a physical education requirement.

Band, orchestra, and choir ensembles each take turns touring a foreign country once every year, during spring break.

Band students have the opportunity to audition to participate in the Illinois Music Educators Association (ILMEA) annual festival honors ensembles.

This organization's chapter, International Thespian Society Troupe #2062, promotes theatre quality at Homewood-Flossmoor.

Activities of the group include monthly meetings, improving the theatre, attending plays and participating in festivals.

The school sponsors interscholastic teams for young men and women in basketball, cross country, golf, gymnastics, soccer, swimming & diving, tennis, track & field, volleyball, and water polo.