Chester had five academy graduates, two players aged under 18 and a couple of trialists in their ranks, but they were more than holding their own in the first quarter of the match.
Liverpool then started to assert their authority on proceedings, with Shenton keeping out Origi's shot at the expense of a corner, from which Scott Burton had to scramble the ball off the line to prevent an own goal.
Fabinho's shot from the edge of the box came back off the upright as the pressure continued to grow, and it eventually told as Wilson dinked the ball over Shenton after Alberto Moreno's initial shot had been saved by the recently-signed keeper - one of nine new recruits for Chester.
Wilson left a further mark on the game by again keeping his cool in front of goal when this time played through by Curtis Jones, tucking the ball out of Shenton's reach into the bottom corner.
Chester's tired legs told in the second half as a Liverpool side showing 11 half-time changes started to run away with things, bagging their third via a Milner penalty three minutes into the second half after Seyi Ojo was brought down by Shenton.
Sturridge played Ojo through for that third goal and he netted the fourth with a composed finish, with Keita closing down high up the pitch creating the opening.
The game's fifth and best goal followed two minutes later through Kent, who sent the ball flying past Shenton from 20 yards when making some space.
Keita then miscued a shot high and wide from a promising position and Sturridge chipped an effort onto the roof of the net, while Ojo's drive was parried away.
One worry for Jurgen Klopp was a knock picked up by Ings, but the striker did not let that faze him as he slotted the ball home following a smart backheeled pass from Milner.
Sturridge rounded off the scoring late on thanks to a curler from the edge of the box, capping a positive first summer outing for Liverpool.
CHESTER FC (4-4-2): Shenton; Smalley (Thomson 58'), Moran, Howson (Marsh-Hughes 78'), Pritchard (Downes 70'); Roberts (Noble 46'), Burton (Brown 70'), Stopforth (Murray 65'), Mahon (Mooney 46'); Hughes (Hellawell 49'), Archer
LIVERPOOL FIRST-HALF XI (4-3-3): Karius; Clyne, Gomez, Phillips, Moreno; Fabinho, Jones, Woodburn; Wilson, Solanke, Origi
LIVERPOOL SECOND-HALF XI (4-3-3): Ward; Robertson, Klavan, Chirivella, Camacho; Milner, Keita, Kent; Ojo, Ings, Sturridge