In search of his insurance payout, Frank retraces the path of an epic bender and finds himself on a wild goose chase through Chicago. Meanwhile, Fiona and Gus make a spur-of-the-moment decision that leads them to city hall. Plus, Lip visits Amanda and her family in Miami; Carl starts a new job as a drug dealer; Ian begins stealing suitcases from the airport baggage claim; and Debbie crushes on a new boy, Derek, who rescues her from a fight.