Which 30 Rock episode features Oprah Winfrey guest-starring as herself on Liz Lemon's flight from Chicago?

The 30 Rock episode featuring Oprah Winfrey as herself on Liz Lemon’s flight to Chicago is “Believe in the Stars.”

In the episode, Liz travels to Chicago for jury duty because she is still registered to vote there. Jack gives her a powerful sedative for the flight, and Liz believes the woman seated beside her is Oprah Winfrey. She becomes convinced that Oprah will visit 30 Rock and help settle the escalating conflict between Jenna Maroney and Tracy Jordan.

The episode originally aired on November 6, 2008, as the second episode of season three and the 38th episode overall. Winfrey did film a guest appearance, making this a genuine celebrity cameo rather than a purely fictional reference. The story also parodies the heightened excitement surrounding her public persona.

The central joke is that Liz’s Oprah encounter is a hallucination caused by the sedative. The passenger is actually Pam, a 12-year-old girl played by Raven Goodwin. Pam nevertheless helps Jenna and Tracy resolve their argument, so the imagined celebrity’s emotional impact becomes real in an unexpected way.