Donna Jensen (GWYNETH PALTROW) has always desired to get out of her little town of Silver Springs, NV and is inspired by former flight attendant turned famous motivational speaker Sally Weston (CANDICE BERGEN) to follow one's dreams.
Donna gets the chance when she joins Sierra Airlines, a small commuter operation, and is taught how to be a flight attendant by seasoned veteran Sherry (KELLY PRESTON). They're soon joined by Christine (CHRISTINA APPLEGATE) and the three become fast friends. Yet, Donna aspires to move on to a bigger airline and gets Christine and Sherry to join her in applying for jobs with Royalty Airlines.
She and Christine are accepted, and begin studying under the direction of John Whitney (MIKE MYERS), the airline's director of flight attendants. Despite Donna being the better student, Christine gets the better assignment, while Donna gets the Cleveland commuter route with gay attendant Randy (JOSHUA MALINA). Once there, however, she runs into a former acquaintance and law school dropout, Ted (MARK RUFFALO), who's now going back to school.
They quickly become lovers, but Donna still wonders why she didn't get a better assignment. As she seeks out the help of Sally who's now her mentor, Donna must decide between love and furthering her career.