The story is about a cricket from Connecticut named Chester who gets caught on a commuter train heading for New York. After stumbling on the subway, Chester ends up in Times Square. Mario Bellini, who helps his parents run a financially struggling newsstand, finds Chester and takes him to the newsstand, as he wants to keep the cricket as a pet and for good luck. Mama Bellini is concerned that the cricket will give the family germs, but Papa Bellini is more easy-going about the cricket's presence. At the newsstand, Chester meets Tucker Mouse and Harry Cat, who spend their time scrounging the city for food and other thrown away items. They show him Times Square, which Chester finds overwhelming. During the story, Chester reveals his musical chirping talent. Mario takes Chester to Chinatown (via the 1 train), where he buys Chester a cricket cage from the Chinatown shop owner Sai Fong.
At one point, Chester accidentally eats a two dollar bill from the newsstand cashier. Mama Bellini wants Chester to go, but Tucker gives part of his coin collection that he's collected from scrounging to save Chester and replace the money. Later in the story during a party that Chester, Harry, and Tucker are having, they accidentally set fire to the newsstand. The fire is put out, but Mama Bellini is extremely angry, accuses Chester of being an arsonist, and demands that Mario get rid of Chester, much to the boy's dismay. However, at the right moment, Chester chirps Mama Bellini's favorite song, which she sings along to and which also leads her to change her mind. It soon becomes clear that Chester has a perfect memory for music, as he chirps opera selections, which surprises Papa Bellini.
Later, Chester chirps classical music pieces and hymns for a music teacher, Mr. Smedley, the Bellini's best newsstand customer, who is impressed and writes a letter to the New York Times about it. This is printed in the newspaper, and brings attention to the newsstand when Chester starts playing concerts there. This causes the poor fortune of the newsstand to turn around, and the Bellinis' sales quickly pick up.
Mario senses that Chester has become unhappy, and says out loud that he wishes Chester hadn't come to the newsstand if he wasn't going to be happy. This makes Chester decide that he wants to return to the countryside. He tells Tucker and Harry this, and Tucker tries to convince Chester to stay. However, Harry says that Chester should do what he wants with his life and stop the concerts if he isn't happy.
With the advent of fall, Chester decides to go home to Connecticut. He gives a final concert that causes Times Square and blocks of New York City to fall still, with everyone stopping to listen to the music. Mario plays one last time with Chester at the newsstand after that last concert, and falls asleep after a while. Later that same night, after Chester gives a farewell chirp to Mario, Harry and Tucker take Chester to Grand Central Terminal so that Chester can hop on to a train. At Grand Central, they all say good-bye. Later, when Mario wakes up as his parents have returned, he realizes later that Chester has gone home, but accepts this by saying: "And I'm glad." The story ends with Tucker telling Harry that maybe they'll visit the country one day, "in Connecticut".