McSheffrey said that he still has the passion to play regular football and was glad to be given the chance to do so at Chesterfield.
"I could have just seen out my contract at Coventry and picked up my wages every month but the manager here has given me the opportunity to play football," he told the club's official website. "I plan on taking the opportunity with both hands.
"The squad is very impressive and there's a good feeling about the place. The manager has a philosophy of total soccer and the lads play some good football. It's a club that's only going one way.
"It's good for both parties because it gives me an opportunity to start playing again and the club can take a good look at me over the next few months. There's a strong possibility that it could be turned into a permanent arrangement."
McSheffrey scored 17 goals in 104 league appearances for Coventry.