A look at the scoreline suggests Chester were unfortunate to take something from the game but that wasn't really the case until the final quarter of a strange game.
Eastleigh took a deserved lead in a first half that saw both sides reduced to 10 men and two goals in the space of five minutes in the second period looked to have completed the job.
Chester did have a couple of chances after the break but those two quick-fire goals seemed to have finished them off.
Steve Burr's men got one back with 12 minutes to go and Eastleigh, who had taken their foot off the gas, found themselves hanging on grimly after another goal in time added on.
Chester made the trip to Hampshire in decent form and on a high following the rip-roaring FA Cup win at Stockport County.
Five wins from eight league games had helped them reach 13th in the table and the manager has been making positive noises about the progress his squad has made.
Burr had to make one enforced change with centre back Michael Kay, who has been in excellent form, starting a three-game suspension so Matty Brown started for the first time since late August
Matty Hughes made the final appearance of his loan spell although Burr will hope to convince Fleetwood Town to extend the arrangement and Ibou Touray was included on the bench having been on trial with Oldham Athletic.
Eastleigh owner Stewart Donald has spent somewhere in the region of £3 million since taking control in 2012.
His investment delivered the Conference South title last term and he put his hand in his pocket again over the summer to fund some high-profile additions.
Eastleigh were mooted as dark horses for promotion in the close season but some disappointing results on the road had undermined an excellent home record.
Richard Hill and his side had taken 21 points from a possible 27 with five of those six wins had coming against teams in the bottom half.
James Constable, one of those big-name summer captures, returned in the sole change to the side that beat Kidderminster in the FA Cup.
Chester could have conceded in the second minute when the home side created an overlap down the right and Dan Spence's cross found Craig McAllister but Brown cleared his goal-bound header off the line.
Eastleigh started like a team high on confidence and the movement between the front four posed real problems for the Blues.
Sean McConville did have a chance on 10 minutes after some smart work from Hughes but his shot lacked conviction and the home side continued to press.
Constable got the ball stuck under his feet in a promising position and Stuart Fleetwood forced Jon Worsnop into two saves in quick succession.
Chester couldn't get into the game and would have been relieved to get to 20 minutes without conceding but soon found themselves behind.
Spence found Jai Reason and he rolled the ball into McAllister, who teed up Ben Strevens and Worsnop saved his initial shot but he followed up to put his side into the lead on 25 minutes.
Home keeper Ross Flitney escaped when he appeared to have handled outside his area as the Blues tried to respond but Strevens should have scored again moments later when he wasted a free header.
McConville was booked for a high challenge on Spence, prompting Hill to lose his cool, and Chester then lost Craig Mahon, the winger limping off to be replaced with Peter Winn.
Five minutes before the break and the game, which had been well natured enough, exploded as Hughes lost his head after Dean Beckwith had hacked him down.
Referee Adam Bromley gave a free kick and looked set to book the defender but Hughes defined the seven centimetre difference in height to aim a headbutt towards Beckwith.
Mr Bromley switched cards and sent off Hughes along with Beckwith, who had grabbed the on-loan forward around the neck.
Chester were still awarded the free kick and should have levelled when Rooney's cross found Craig Hobson but he poked past the post from six yards out.
Eastleigh had the final chance of the half when McAllister was slipped into space but he dragged wide after Brown's saving tackle to ensure the deficit remained one goal.
McAllister wasted another excellent chance two minutes into the second half when Michael Green floated a cross to the back stick but the unmarked forward headed over.
Chester survived and began to come more into game with Winn having a deflected shot saved before he beat the defence and found Hobson but he poked wide under pressure.
Hobson had an even better chance on the hour mark with Winn again the provider but the forward failed to keep his cool and the onrushing Flitney saved with his feet.
Chester paid the price on 61 minutes when Eastleigh doubled the lead from the spot after Reason got the wrong side of Heneghan and the full back clipped his heels.
Mr Bromley had a simple decision to make and Fleetwood converted the penalty to give his side a two goal cushion.
Four minutes later and the home side were in again, Reason again involved as he clipped a pass into the box and McAllister had far too much time and space to stab the ball past Worsnop.
Hobson came off for Jamie Menagh for the final 20 minutes, showing the dearth of striking options in the squad, and Eastleigh began to relax.
Chester plugged away and pulled a goal back out of nothing on 78 minutes when Menagh found Winn and he clipped a cross to the far post for McConville to steer the ball into the net.
A comeback looked unlikely but would have been a lot more possible had Menagh been able to connect with Rooney's low cross with the 10 minutes to go.
Eastleigh were far from convincing in the closing stages and Flitney made an important save on 85 minutes after Rooney's clever free kick had released Menagh.
Chester continue to go forward and got another one back in time added on when Kingsley James created space and his left foot shot whistled past Flitney.
Eastleigh, who had been well in control, now found themselves clinging on and were grateful for the full time whistle while the Blues will rue the mistakes and sloppiness that left them chasing the game.
Chester FC: Worsnop, Heneghan, Brown, Charnock, G Roberts, Rooney, James, Mahon (Winn 34), McConville, Hughes, Hobson (Menagh 69).
Subs: C Roberts, Harrison, Touray.
Goal: McConville 78, James 90.
Sent off: Hughes 39.
Eastleigh: Flitney, Spence, Beckwith, Evans, Green, Fleetwood, Stanley, Strevens (Odubade 69), Reason, McAllister (Wright 69), Constable (Todd 46).
Subs: Reid, Helm.
Goal: Strevens 25, Fleetwood 61 (pen), McAllister 65.
Sent off: Beckwith 39.
Referee: Adam Bromley (Plymouth).