Despite the defeat, there were several bright spots for the home side, however.
Chesterfield welcomed back Jack Hartley into the squad who equalised with a fine goal, and Cameron Gordon continued his excellent form post injury with an all action performance at right-back.
On balance of play, the 3-1 half-time deficit was possibly a little harsh on the hosts, but in the second-half the away side showed their class to put the game to bed.
Josh Beardsley pulled a goal back for Chesterfield but York were able to seal the points with two further goals for a 5-2 final score.
The result leaves Chesterfield as they were before the weekend’s fixtures, sitting in tenth place.
Captain Jon Moores said: “I thought we looked pretty good for large parts of the game, but they did the basics very well, which makes a difference at this level.
"It’s not one or two big moments in a game that you need, but lots of little things done consistently well and that’s what we lacked.
"We should still be proud of our effort and attitude, we didn’t roll over and hand them the win but we know need to add that little bit of care around our basic skills”.
Chesterfield host high-flying Stockton on Saturday, before travelling to mid-table Brigg on Sunday.