But in the 69th minute, Coventry's homegrown captain Jordan Willis fired home from close range to put his team on course for three points and to put some breathing space between themselves and the relegation zone.
Despite being on top for most of the match, City had failed to make the most of their dominance and too often their final ball was either wayward or never materialised as they occasionally overplayed in the final third.
Chesterfield, on the other hand, looked to shoot whenever they got a sniff of the Coventry goal.
Striker Ched Evans had a hat-trick of opportunities midway through the second half. The first he shot wide and was then foiled by two solid saves by City keeper Lee Burge before Willis struck and then substitute Andy Rose sealed a home win in the 81st minute.
Coventry full-back Lewis Page was given a red card in injury time for picking up a second booking.