Chester, who will be pitting himself against a couple of childhood friends, was on the books at Old Trafford as a youth but the closest he ever got to the first team was a second-half substitute appearance in a League Cup semi-final against Derby.
Loan spells at Peterborough, Plymouth and Carlisle gave him a taste for competitive football and in January 2011 he signed for the Tigers.
The 24-year-old was an instant success in East Yorkshire and was a major reason for the club's unexpected promotion to the top flight last season.
He has retained his place in the first-choice XI despite early-season injury problems and will get the chance to come up against his former employers when they visit the KC Stadium on December 26.
It is a big fixture for Chester on both a personal and professional level.
"Manchester United was the fixture I looked for when the games came out at the start of the season," he said.
"I spent a long time there and I owe them an awful lot.
"Perhaps I have a little bit of point to prove but I don't hold any grudges and I am very thankful for the 10 or 11 years they gave me. But it would be nice to show people how I have done. Getting into the Premier League was my first aim and I want to stay here now."
Depending on how Red Devils boss David Moyes deploys his resources over the festive period, Chester could also find himself up against two very familiar faces.
"I have known Tom Cleverley since I was eight, and used to train with him and Danny Welbeck," he added.
"Me and Danny used to come up against each other pretty much every day - I still have a scar on my face where he kicked me on the head. I am proud of what he has managed to do at United.
"Watching the lads play in the Champions League has made me target that as an ambition now. I know it's a long shot and a long way off but you never know."
Hull manager Steve Bruce is another with ties to United, though he fared slightly better at the club and was captain during one of their most successful periods under Sir Alex Ferguson.
Despite that, he has never beaten his old team as a manager.
Whether or not that changes this week, he is relishing the day.
"I've never beaten them so it's not a game I pencil in straight away," he confessed.
"But for all of us at Hull, what better time to have them come here than on Boxing Day?
"Traditionally that's the biggest and best gate you have. And the same for Manchester United.
"It's a great occasion for all of us...over the Christmas period hosting the champions when they are running into a bit of form.
"Let's enjoy the challenge and see if we can take something off them."