Her acting career began in 2009 and she received her breakout role two years later, co-starring as Dalia Royce in the ABC sitcom Suburgatory.

Chaikin was born in Santa Monica, California, to a cardiologist father and a psychotherapist mother.

[3] During this time she played a variety of sports, including volleyball, softball, basketball, and soccer.

The same year, Chaikin starred alongside Miley Cyrus in the film adaptation of Nicholas Sparks' The Last Song, initially released in the US on March 31, 2010.

[6] In 2011, Chaikin was cast as Dalia Oprah Royce in the ABC sitcom Suburgatory alongside Jeremy Sisto and Cheryl Hines.

[17] Chaikin appeared in the 2012 independent film My Uncle Rafael starring John Michael Higgins.

[22] She plays the programmer Darlene, one of the show's central characters, who is a member of the fsociety group and writes malicious rootkit code.

She served as emcee of NAMIWalks in both 2016 and 2017, as well as raising money for the organization and matching incoming donations.

[35] On September 3, 2018, Chaikin announced that she was engaged to her longtime boyfriend, television director Ryan Bunnell.