The live auction will be hosted by Prop Store, a props and costumes auctioneer based in London and Los Angeles, on 26 and 27 August.
Other items include a helmet worn by Tom Cruise in Top Gun and boxing gloves used by Sylvester Stallone in Rocky.
Cliff Booth, Pitt’s character in Quentin Tarantino’s film, drives a blue Volkswagen Karmann Ghia, which is estimated at $20,000 – $30,000.
DiCaprio’s Rick Dalton, meanwhile, gets chauffeured in a yellow Cadillac Coupe de Ville, with an estimate of $45,000 – $55,000.
Cruise’s Top Gun helmet is expected to reach $50,000 – $70,000, while Stallone’s Rocky gloves have an estimate of $12,000 – $16,000.
An 11-foot model of the Alien Nostromo starship is expected to be the most expensive item, reaching $300,000 – $500,000, according to a sampling published by Variety.
The sale will also includes one of Jennifer Lawrence's costumes from The Hunger Games, as well as items from Thelma and Louise, Ghostbusters II, Raiders of the Lost Ark, and more.