TripAdvisor, an online travel information resource, is co-sponsoring a screening of "Roman Holiday" on Tuesday night, and "Planes, Trains and Automobiles" on Wednesday.
Suitcases for Kids, a charity that helps youth in foster care by providing them with luggage and backpacks, will co-host the event.
Attendees are encouraged to bring a piece of new or lightly used luggage to donate. Items collected will be distributed to local kids in foster care by the California Youth Connection, a non-profit foster youth advocacy group.
Moviegoers should also bring blankets, as the screenings will have limited seating and be shown in more of a "picnic atmosphere," according to event planners.
The films will be projected on to a 40-foot by 20-foot inflatable screen.
The square will open to the public at 6 p.m. on both nights, with movies scheduled to start at sundown.