The Spireites opened the scoring in the eighth minute when new signing Gary Roberts pounced on a loose ball after an initial shot had been blocked.
Town were soon level, though, as their summer signing Martin Paterson played in Danny Ward and his deflected strike beat home goalkeeper Tommy Lee.
The Terriers, playing their first friendly of the summer, fielded a completely new side after the break.
And the hosts took advantage as they snatched victory shortly after the hour mark through triallist Jamie Devitt's superb curling free-kick.
Former Hull winger Devitt, 23, had only entered the action as a substitute a few minutes earlier.
Huddersfield manager Mark Robins was satisfied with his side's workout.
He told the club's official website: "On the football side of things I thought we looked ok at times, but Chesterfield were better than us; they are ahead of us in their games schedule.
"There are certainly a lot of things to work on technically and tactically; that's clear. That will come later on.
"However, in all fairness you can't read too much into the first friendly - this stage of the season is all about what you've got in your legs. We were ok without being sharp."