Having previously earned a point at top dogs Scunthorpe and form team Rochdale, Ian Rush's men knocked Macclesfield off their fifth placed perch with a stirring comeback.
Trailing to Mike Sheron's 20th minute strike, when the former Manchester City striker turned neatly to crash a shot between Chris MacKenzie's legs from six yards, Chester were a different proposition in the second half.
Twice they went close when Michael Brown and then Michael Branch looped headers inches over the bar.
But they were not to be denied when Stewart Drummond crashed home an 18-yard half volley which left Steve Wilson stranded.
Macclesfield responded when on-loan centre back Greg Strong curled a 25-yard free-kick on to the crossbar only for the ball to fly to the other end for former Stockport playmaker Kevin Ellison to curve a 25-yard drive into the top corner.
Again Macclesfield tried to regroup, their 14-goal striker Jonathan Parkin seeing a close-range header brilliantly tipped on to the bar by the alert MacKenzie.
Macclesfield had played the better football in the first half and should have sealed the game before the break.
On 41 minutes Danny Whitaker saw a 20-yard lob sail inches over the bar and on the stroke of half time Matthew Tipton left MacKenzie wrong-footed with a delicate chip only to see the ball sail agonisingly wide.
But Macclesfield sat back after the break, fatally trying to protect their narrow lead.
They appeared to have sealed the game when Whitaker fired home the rebound after MacKenzie had blocked a Tipton shot but it was disallowed for offside.