The 31-year-old had been training with the club following his departure from Sky Bet League One side Coventry.
If McSheffrey's short-term spell is a success the Spireites could extend his contract until the end of the season.
McSheffrey told the club's official website: "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. 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."