Chalupny joined River Cities Futbol Club of the Women's Premier Soccer League. WPS, 2009–2011 On September 16, 2008, Chalupny was one of the three players drafted for Saint Louis Athletica in the 2008 WPS Player Allocation of national team members, with the new league starting play in April 2009. She scored the first home goal of the season off of a corner kick in a 1–0 win against FC Gold Pride. She was team captain, made the All-Star team, and was nominated for WPS's Player of the Year award the same year. During the 2010 and 2011 seasons, she played for the Atlanta Beat and appeared in 15 and 17 games respectively and scored 2 goals in each season. Chicago Red Stars (WPSL-Elite) and AIK Fotboll, 2012 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. On August 8, 2012, she joined AIK Fotboll Dam in the Swedish Damallsvenskan. Chicago Red Stars (NWSL), 2013–2015 On February 5, 2013, she rejoined the Chicago Red Stars in the new National Women's Soccer League. Chalupny captained the Red Stars during the inaugural season, played 18 matches and scored 5 goals, the highest scored by a member of the team; and was named to NWSL 2013 best eleven. 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. At the end of the 2015 National Women's Soccer League season she retired from professional soccer. International A member of the U.S. national under-16, 19 and 21 teams, Chalupny earned her first cap for the senior team on March 7, 2001 against Italy. She scored her first goal for the U.S. senior team on May 9, 2004 against Mexico. Although she predominantly played left back at the 2005 Algarve Cup, she also played as an outside midfielder. In January 2006, Chalupny suffered a concussion after two blows to the head in a game against France. She was ordered by her doctors to take several months off, and did not return to national team play until July 2006. She started at midfield in all six of the United States' games at the 2007 FIFA Women's World Cup, and scored two goals, one of which was the