He is first seen very early on in the game when he gives Professor Layton and Luke a bit of information about the train while Professor Layton is investigating his beloved mentor, Dr. Andrew Schrader. Chester tells them history about the train and redirects them to other members of the train's staff. He then tells them about the hugeness of the customers the Molentary Express' dining car gets almost every day. As Professor Layton and Luke explore the "Cruise Ship on Rails" they encounter many colorful characters and eventually find themselves with a vacant seat in the dining car. When they almost sit down Babette, a pompous windbag of a woman, says she is much more important and deserves the seat more. She then takes the seat and Professor Layton and Luke wait even more time to eat the delicious food the Molentary Express has to offer. Later, while they investigate the observation deck, they see glorious scenery and then go back to the dining car. The dining car then has opened seats and then have their long awaited dinner.
Chester is on the Molentary Express car 5. He gives Professor Layton and Luke one puzzle while they look for clues on the train. The first puzzle is "Dining Couples". He then later gives them another puzzle when they eat. This puzzle is "Luke's Big Dinner"
Peek into the Molentary Express's dining car, and you're likely to see Chester, server and host extraordinaire. His commitment to catering to customers' needs contributes to the Molentary Express's lavish reputation.