After singer Lily Lamont and her hoodlum boyfriend, Charlie Cooper, steal a valuable necklace known as the "Czarina's Tears," from Phelps's jewelry shop, Phelps orders insurance company manager J. W. Ridgeway to retrieve it. Despite the misgivings of police Lieutenant Eckhardt, Ridgeway hires suave Barry Drake, whom Eckhardt believes to be a thief himself. Barry goes to the club where Lily works and finds Charlie, after which he searches Charlie's apartment. Charlie surprises Barry, but Barry prevails during their struggle and tells Charlie he will split the reward money with him if Charlie gives him the necklace. Charlie refuses, but Barry finds the necklace anyway and returns it to Ridgeway the next day. After Ridgeway and Barry leave, Phelps arrives and tells Eckhardt and Ridgeway's intrepid secretary, Dale Harrison, that the necklace Barry returned is an imitation. Eckhardt and Dale search for Barry, whose valet, "Whitey" Whitehouse apprises him of the situation. Barry and Whitey go to the train station, as Barry had found train tickets in Charlie's apartment, and they board the same train. Dale follows them onto the train and tells Barry she is a reporter when he finds her searching his berth later. They keep a wary eye on each other and soon arrive in Cincinati, where Eckhardt joins Dale and Lily meets Charlie. Dale goes to Lily's room, but Charlie is not fooled by her maid disguise, and he ties her up before he and Lily leave. Barry and Whitey arrive and free Dale, then give her the slip again when she tells them where Charlie and Lily are going to fence the necklace. The thieves go to Mondoon's antique shop, but Mondoon tells them that the necklace is too hot for him to handle. He recommends someone in New Orleans who may be able to help, after which they are confronted by Barry, Whitey and Dale, who have managed to catch up. Lily and Charlie escape by foot, but then must reverse the chase when the others drive off with Charlie's car and Lily's suitcase, thereby taking the cold cream jar in which Lily has hidden the necklace. Barry, Whitey and Dale travel to New Orleans, but run out of gasoline on the way. They stop at the cabin of a hillbilly family and Dale and Barry flirt, while Whitey goes to get gas. Whitey finds Dale's mislaid purse, and the men learn her true identity and occupation. Barry and Dale quarrel, after which she discovers that one of the children has found the necklace in Lily's suitcase. Dale tries to give it to Barry, but just then, Eckhardt appears, and Barry retreats with Whitey. Barry has a change of heart and goes back for Dale, but Charlie and Lily have already found the cabin. After a series of struggles, chases and searches for the cold cream jar, Dale escapes with the necklace, and Eckhardt arrests the others. Later, Dale returns to the insurance office and replaces the fake necklace with the real one, then, when Eckhardt brings in Barry, Barry is able to present Phelps with the authentic necklace. Eckhardt and Phelps leave, and Barry and Dale plan a trip to city hall to get married during her lunch hour.