A music video of singer Abhijeet Bhattacharya followed. Subsequently, she made her much acclaimed debut with Sudhir Mishra's film Hazaaron Khwaishein Aisi in 2003. The role got her wide acclaim: a Washington Post review noted her for giving "her character a deep sense of dignity and decency." After that Chitrangada acted in the 2005 film Kal: Yesterday and Tomorrow.
She took a break from acting from 2005 to 2008. In 2008, she made her comeback with the leading role opposite Sanjay Suri in the Director Onir's romantic-comedy, Sorry Bhai!. Its release over the weekend of the Mumbai terror attacks proved disastrous at the box office.
In Sudhir Mishra's movie Yeh Saali Zindagi (2011), Singh played the role of an aspiring singer from Delhi who goes to Mumbai to get fame and money.
In 2012, she performed an item number in Shirish Kunder's Joker.
Chitrangada Singh was married to Golfer Jyoti Randhawa. Chitrangada and her husband separated in 2013 and then formally got divorced in April 2014. The couple has a son named Zorawar; his custody has been granted to Chitrangada.
In 2015, She again performed a special song with Akshay Kumar for the second time in his film Gabbar is Back.
