"[2] She then went on to play soccer at Nerinx Hall High School where she was also on the Honor Roll her sophomore, junior, and senior years.

She also played for club soccer team, J.B. Marine S.C.[3] She was named NSCAA and Parade All-American as a junior and senior.

[4] Chalupny played for the University of North Carolina at Chapel Hill from 2002 to 2005 and won an NCAA championship title with the Tar Heels as a sophomore in 2003.

[3][5] After missing much of her freshman season due to injury, she played in 16 games, scored three goals and served seven assists.

[3] During her final year with the Tar Heels, she scored ten goals and served eight assists playing as a midfielder.

[4] In April 2006, Chalupny joined River Cities Futbol Club of the Women's Premier Soccer League.

[6] After the folding of the WPS in early 2012, she played for the Chicago Red Stars in Women's Premier Soccer League Elite, appearing in ten games and scoring five goals.

[10] In 2014 National Women's Soccer League season, Chalupny captained Chicago Red Stars to fifth place, played in a team high of 23 matches and 2003 minutes, and scored five goals.

She played every minute of five matches in 2009, captaining the U.S. team in a 1–0 win against Germany after co-captain Christie Rampone became pregnant.

From 2009 to November 2014, Chalupny was not called to play for the United States women's national soccer team due to a history of concussions.

[15] National team head coach Jill Ellis selected Chalupny as part of the roster for the 2014 International Tournament of Brasilia.