She performed lead roles in The Visit by Friedrich Dürrenmatt and Crimes of the Heart by Beth Henley.

[6] While in high school, Fineman impersonated a peafowl on the Late Show with David Letterman after winning a bird calling competition.

[8][9] After graduating from college, Fineman moved to Los Angeles,[4] where she performed in The Groundlings troupe's Sunday Company.

[11] In 2018, Vulture critic Luke Kelly-Clyne wrote that after seeing Fineman do impressions of Meryl Streep and others, "As I found out, that extra bit of genius she possesses – that intangible thing that takes a good impression to a great impression – is rooted in her ability to create entirely original characters who feel as real as anyone you've ever met," concluding, "Chloe Fineman is absolutely one of the most talented new performers right now, and she's long overdue for a break.

[18] Alongside Yang and Heidi Gardner, Fineman was cited as the season's best performer by Andy Hoglund at Entertainment Weekly.

[20] In 2022 she had a supporting comedic role as a wedding planner in the romantic comedy Father of the Bride,[21] and in the same year she portrayed Marion Davies in the Damien Chazelle-directed film Babylon.