Kwan began skating at age five and won her first competition two years later. In 1994 she landed the alternate spot on the U.S. Olympic team and the following year placed fourth at the world championships. In 1996, sporting a new, more grown-up look, she won her first U.S. and world titles. After a growth spurt that added both height and weight, Kwan finished second to Tara Lipinski at the U.S. and world championships in 1997. She entered the 1998 Olympic Games in Nagano, Japan, as the gold-medal favourite, having defeated Lipinski at the U.S. championships earlier in the year. Lipinski, however, won the closely contested event, and Kwan had to settle for a silver medal. She captured a bronze medal at the 2002 Games in Salt Lake City, Utah, and the following year won her fifth world championship (1996, 1998, 2000–01, 2003). In 2005 Kwan claimed her ninth U.S. title, tying a record set by Maribel Vinson in 1937. Later that year, however, she finished fourth at the world championships, marking the first time since 1995 that she had not won a world medal. She qualified for the 2006 U.S. Olympic team but was forced to withdraw after she suffered an injury during her first practice at the Games in Turin, Italy. Kwan did not compete during the 2007 and 2008 seasons while pursuing studies at the University of Denver.

In November 2006 Kwan was appointed envoy for public diplomacy by the U.S. State Department. Her autobiography, Michelle Kwan: Heart of a Champion, was published in 1997.