Chester was on the books at Old Trafford as a youth player but the closest he got to the first team was a second-half substitute appearance in a League Cup semi-final against Derby.
However, after loan spells at Peterborough, Plymouth and Carlisle, the 24-year-old joined the Tigers in January 2011 and was an integral part of the team that enjoyed promotion to the top-flight last season.
Despite injury concerns at the start of the current campaign, Chester is in fine form and will now welcome his former employers when they visit the KC Stadium on December 26 - a game which will be shown live on Sky Sports 1 HD from 12.30pm.
"Manchester United was the fixture I looked for when the games came out at the start of the season," Chester 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."
Watch Hull City take on Manchester United live on Sky Sports 1HD from 12.30pm on Boxing Day, or for just £4.99 with a NOW TV day pass.