Principal photography began in downtown Los Angeles, where the interior editorial offices of the Chicago Sun-Times were constructed inside a vacant office building. Production designer Steven Jordan had undertaken a technical scout of the real Chicago Sun-Times offices to gather design information which he blended into the set.

Jordan and his team of art directors and set decorators and dressers strove to make the space as realistic a news room as possible. "The Chicago Sun-Times set was a result of visiting a number of papers here in Los Angeles and also in Chicago," he explains. "We blended a mixture of two types of newsrooms: one, which is newer and well manicured, and the other which is just piles and piles of hysteria."

The majority of the film takes place at South Glen South High School, a fictional school whose name is a derivation of Chicago’s own North Glen North High School. Two schools in Southern California were used for all these scenes: John Burroughs Junior High in the Hancock Park area of Los Angeles, and the William S. Hart High School in Newhall in the San Fernando Valley. Both schools were closed for summer recess during filming.

A beacon for location managers, John Burroughs Junior High has been utilized for years in dozens of movies, from "Pretty in Pink" to the recent "Killing Mrs. Tingle." The producers chose the brick-covered Burroughs school primarily for its Eastern U.S. look, while the William S. Hart High School was chosen primarily for its athletic facilities.

Wishing to avoid the creative trap of making the environment too contemporary, the producers brought on respected costume designer Mona May, whose work on the comedies "Clueless," "Romy and Michelle’s High School Reunion" and "The Wedding Singer" showcased some of her colorful costume designs.

Drew Barrymore’s character set the tone of the film. "Josie goes through several different transformations in the movie," explains May. "She starts off as an uptight twenty-five-year-old, so her clothes are very put together, very clean, very neat. Then she gets the assignment to go to the high school, and since she really doesn’t know what’s going on right now with teenagers, we went a little way out and gave her this kind of Spice Girl look." May explains that Josie is either overdressed or underdressed, but eventually finds her own personal style. "It’s simple and sweet. The movie has a great message about that, which is ‘Be yourself.’"

The theme of South Glen South’s huge prom, "Meant for Each Other: Famous Couples Throughout History," brought out some of May’s most outrageous costumes, including Peanut Butter & Jelly, Joseph & Mary, Uncle Sam & Betsy Ross — and the Denominators’ costume, which grouped them in a chain strand of DNA.

Though the bulk of the movie was filmed in Los Angeles, the crew traveled to Chicago to capture key exterior locations, including the Chicago Sun-Times building and Navy Pier. For the latter locale, the production brought in a special ferris wheel, as Navy Pier’s was judged too large for the scene.