Friendship
The Cricket in Times Square relays a strong message about the power of friendship. Friendship crosses all kinds of boundaries, and in this book even the unlikeliest of individuals become friends. Chester Cricket develops a deep friendship with a human, Mario, and Mario crosses cultural boundaries when he befriends Sai Fong, an older Chinese man. Chester's friendships make his time in New York City worthwhile; without the help of Harry and Tucker, Chester would have been lost, confused, and lonely in the big city. Having a good friend by your side can make even a scary situation much more bearable.
Beyond the Comfort Zone
To a cricket from rural Connecticut, New York City is about as alien of a place as it gets. Throughout the course of the story, Chester is repeatedly thrown out of his comfort zone and must learn to adapt to countless new and scary situations. These tests of courage show off Chester's strong character, and he becomes even better because of them. Chester grows greatly as a result of venturing beyond his comfort zone, which shows how important it is to give new things a chance.
Everything is Not What it Seems
Everyone and everything in this story has more to it than meets the eye. No one expects Chester, a cricket, to become New York City's latest and greatest musician, but he has talent in him that is not immediately evident. Harry and Tucker, a cat and a mouse, should not be best friends, but they are. Even the animals themselves are more than meets the eye, because they can talk and think just like humans would. Selden strives to create a sense of the unexpected in his stories, and The Cricket in Times Square definitely shows that everything is not what it seems.
Morality and Responsibility
Both Chester and Mario have sound moral values, accepting the blame for things that are their responsibility and showing true regard for the well being of others. Mario stoically accepts his mother's blame for all the accidents that happen because of Chester, since he had agreed to be responsible for the cricket. In turn, Chester takes the punishments he is given as well, wanting to be fair to Mario. No matter what, Chester does not want to bring any harm upon the Bellinis who have shown him so much kindness, which exemplifies his strong values.
Home
Chester is constantly longing for the familiarity of his home back in Connecticut. But the more time Chester spends in New York, the more fluid the idea of "home" becomes. In many ways, Chester comes to feel at home in New York, despite the busy, bustling city's many differences from the place where he was once comfortable. Home does not necessarily have to mean the place where he has spent the longest time. In reality, home is where you are surrounded by others who love and support you, and that is exactly what Chester has in New York with Mario, Tucker, and Harry. In the end, Chester decides to return to his former home—however, he will always have a different kind of home in New York, too.
Hard Work
The Bellinis are a great example of the value of hard work. They do not have much, but they work hard to support themselves with their newsstand, and are eventually rewarded by the stroke of good luck that finding Chester brings them. Other characters in the story are hard workers, too, including Chester as he works hard to perform concerts to help the Bellinis, and even Tucker, who has worked hard for a long time to amass his life's savings. Good things come to the hardest workers, even though it may take time.
Be Careful What You Wish For
Though Chester's musical genius certainly brought the Bellinis good fortune, in many ways the family and Chester bit off more than they could chew. Their lives changed drastically once the crowds started lining up to hear the amazing chirping cricket, and their family dynamic was not the same as it once had been. This was too much for Chester to handle, too, since he had never performed nonstop like this before, and he had to trade his happiness to help the family that he had come to care for. It is a cautionary tale to be careful what you wish for; some things, like happiness, are more important than fortune.