Striker Scott Boden, who scored twice for Gateshead in a 3-0 win over Town earlier this season, is a transfer target for new boss John Sheridan.
The manager told local press last week that he was hoping to bring in two players, one of them a striker.
The Derbyshire Times understands the two clubs are in talks over Boden's future.
If the Spireites are to prise him away from the Gateshead International Stadium it will require a transfer fee, but with his contract due to run out in the summer, the Heed may look to cash in.
Chesterfield owner Dave Allen has already shelled out for a forward this season - previous boss Martin Allen was permitted to buy Tom Denton from Alfreton for a fee believed to be in the region of £75k.
Boden scored in Gateshead's 1-1 draw at Salford on Saturday, making it two goals in his last two games.
He's fired in 10 in 29 games for the Tynesiders since signing in the summer.
Back in June, Boden told the Derbyshire Times he would love to come back to the Spireites.
In an interview about his former Wrexham team-mate Sam Wedgbury moving to the Proact, Boden said: "Jesus, yeah, it’s the club that gave me my first pro contract and it’s close to my heart.
"In some ways I’m envious of Sam’s move. I’m gutted for the club and surprised they are in the position they now find themselves in, a lot has changed in the last five years, but I’m sure one day they’ll be back up the leagues, where they belong.”
Boden played over 100 times in his first stint as a Chesterfield player and scored 18 goals.
Under Sheridan's management, he earned a League Two winners medal and lifted the Football League Trophy.