The sunshine of Barbados moved one step closer for the Stags as their slim promotion hopes - and the prize of a free holiday to the Caribbean if they reach the play-offs - were kept alive by a late winner.
New chairman James Derry had offered the holiday incentive just before kick-off in a bid to inspire Mansfield to extend their three-match unbeaten run.
But it was Chester who looked inspired as they grabbed an early lead through debutant Brad Maylett and went in search of their first win in four games to keep alive their own outside hopes of reaching the play-offs.
But Mansfield came storming back to stretch their unbeaten run to four games and move to within nine points of a play-off place - condemning Chester to only their second defeat in eight away games.
Mansfield central defender Alex Baptiste was the unlikely hero, heading in a corner eight minutes from time following Simon Brown's first-half equaliser.
Former Stags' favourite David Artell was ruled out of a return to his old club through a head wound, but Maylett, on loan from Boston, did make his full debut for Chester - and made an immediate impact with the opening goal.
A defensive error and a fine finish handed the visitors a ninth minute lead. The recalled Jon Olav Hjelde looked uncertain as he tried to shepherd the ball back to his keeper, and his eventual clearance fell kindly for Maylett to hammer first time into an empty net from an acute angle.
Chester looked dangerous on the break and Maylett should have struck again in the 12th minute when he raced clear onto a long goal kick, but his final tame shot was easily saved by Jason White.
Mansfield dominated possession though and threatened an equaliser through Brown, Barry Colon and Nathan Arnold, before Brown finally raced on to Conlon's perfect pass over the defence, raced clear and finished calmly to level in the 27th minute.
The home side might have taken the lead just before half-time, but keeper John Danby superbly dived low to cut out a deflected Bryan Hodge cross.
With the Stags still dominant, Chester survived a double scare in the 53rd minute. First Simon Marples raced back to prevent Hodge from converting a John Mullins cross.
Then, with keeper Danby struggling to reach a cross from the resulting throw, Jamie Hand threw himself in the way of Arnold's finish to again deny the home side the lead.
On a rare City counter attack, Laurence Wilson forced White into an acrobatic flying save as his 35-yard thunderbolt was tipped away from the top corner by the young keeper.
But the home side continued to dominate and another fine piece of defending, this time from Phil Bolland with a perfectly-timed clearance, stopped Conlon from heading in a cross from substitute Matt Hamshaw.
But the Stags could not be denied in the 82nd minute when another Hamshaw flag-kick was inadvertently flicked on by a Chester defender and Baptiste headed home via the underside of the bar.