A moment of class from John Rooney on 14 minutes finally gave the Blues something to cheer at home and a deserved three points.
Chester kept the ball better, created some good chances and defended well under late pressure from an in-form Macc side, who lost for the first time this season.
Steve Burr's side had needed to produce something to give the home fans reason to believe after the painful defeats to Barnet and FC Halifax Town.
There had been some positive signs on the road, including the first half at Gateshead last weekend, but on the whole performances had been too inconsistent.
Burr made one change from the 2-1 defeat in the North East with Kieran Charnock replacing Danny Taylor meaning Ben Heneghan reverted to right back.
Danny Harrison and Kingsley James shook off knocks to start in midfield, Craig Hobson continued up top having scored in his last two matches and Callum Morris, signed on non-contract forms, was named on the bench.
Macc came into the game unbeaten and brimming with confidence after a 2-0 win over big-spending Eastleigh last time out. Manager John Askey named an unchanged side but there was a return on the bench for ex-Chester City forward Chris Holroyd.
Both managers favour passing football and there was a decent pace about the opening 10 minutes.
Jon Worsnop made a couple of comfortable saves from a George Pilkington header and a low Arthur Gnahoua shot but neither troubled him too much.
Rooney looked sharper back in his favoured number 10 role and he put the Blues ahead on 14 minutes against his former club.
Luke Waterfall bundled over Craig Hobson and referee Richard Wigglesworth awarded a free kick 20 yards out. Rooney whipped the ball around the wall with his right foot and into the top corner to give keeper Rhys Taylor no chance.
Macc attempted to get back on terms but couldn't create much other than Wade Fairhurst's 25-yard strike that Worsnop held.
Rooney had a shot blocked at the other end before a defensive slip allowed Gnahoua through on goal but Worsnop did well to get his hand to the ball.
Chester were the better team and had chances for a second with James flicking Rooney's cross past the post and Harrison screwing a shot wide.
Macc grew frustrated with Paul Turnbull and Andy Halls picking up bookings and the unimpressed Askey made a change before the break with Holroyd coming on.
Burr could have few complaints at the end of the first half, indeed his only gripe might have been that the lead was not more than one goal.
Chester continued to press once the game had resumed and Rooney forced Taylor into a save with a low shot two minutes into the second period.
Macc came back into things but were too wasteful in possession to trouble the defence although there was a nervous moment when Domaine Rouse beat the last man but Worsnop rushed out to clear.
Chances were few and far between over the next 20 minutes with the sides cancelling each other out as the game became less open.
Macc were having more possession but didn't threaten other than two Scott Barrow shots, one sliced well wide and the other from deep into his own half.
Hobson came close to putting the Blues two up on 78 minutes with a brilliant chip from 20 yards but Taylor made a fantastic save to tip the ball over the bar.
Worsnop was called into action after the ball broke to the back post and Holroyd looked certain to score but the keeper made an excellent block.
Macc threw men forward in the final 10 minutes but were unable to breakdown the Blues, who stood tall and strong until the final whistle.
Chester FC: Worsnop, Heneghan, Charnock, Kay, Roberts, Rooney, Harrison, James, Hall (Mahon 70), McConville, Hobson.
Subs: Roberts, Riley, Morris, Iwelumo.
Goal: Rooney 14.
Booked: Kay.
Macclesfield Town: Taylor, Halls, Pilkington, Waterfall, Barrow, Moke (Holroyd 43), Lewis, Turbull, Gnahoua, Fairhurst, Rouse (Haining 80).
Subs: Cowan, Diaz, Branagan.
Booked: Turnbull, Halls, Barrow, Waterfall.
Referee: Richard Wigglesworth (Doncaster).
Attendance: 2,612.
