Antonio Conte made it clear that he is looking for further additions and has made strengthening the wing-back positions a priority before the close of the summer transfer window.
Oxlade-Chamberlain is primarily an attacking player, who was touted to eventually play in a central midfield role by Arsene Wenger. But the England international has been used as a right wing-back since the latter stages of last season and seemed to excel in his new role.
Victor Moses is Conte's only option at right wing-back at the moment and the Italian coach is said to be keen to bring in Oxlade-Chamberlain to challenge the Nigerian for a regular role in the starting lineup. According to the Daily Mail, the Blues are willing to test the water with a £25m bid despite Wenger insisting earlier in the summer that the midfielder is not for sale.
Arsenal are facing a dilemma as the former Southampton starlet is currently in the final-year of his contract with the club and is yet to agree to a new deal. If they choose to keep for the upcoming campaign, the Gunners could end up losing on a free transfer next summer.
Chelsea are not the only club on his trail as Liverpool have also shown interest in taking him to Anfield. Recent reports suggested that the Reds are favourite after Oxlade-Chamberlain hinted at a move by linking a social media post that suggested he was on his way to Merseyside in a £28m deal.
Apart from the Arsenal star, Chelsea are also said to be monitoring Valencia right-back Joao Cancelo as a potential option to challenge Moses for the right wing-back position. The Portugal international has impressed for club and country in the past year and according to Sky Sports, the Stamford Bridge outfit have had him scouted extensively during that period.
The 23-year-old, who is contracted to the La Liga outfit until the summer of 2021, made 38 appearances in all competitions last season. Apart from Chelsea, he has also been linked with Tottenham Hotspur, who are also looking for a right-back following Kyle Walker's move to Manchester City.
Conte is also looking at options for the opposite flank with Marcos Alonso the manager's only option in the left wing-back position. Chelsea were linked with a move for AS Monaco's Benjamin Mendy, but the Frenchman chose to join Pep Guardiola's revolution in Manchester instead.
According to the Sun, Chelsea have now identified Spurs' Danny Rose as an ideal candidate to challenge Alonso for a place at left wing-back and the former Juventus manager has reportedly asked the club's hierarchy to make a £40m move for the England international.
The 27-year-old, who is currently sidelined by injury, is contracted to the north London club until the summer 2021 and reports suggest that Tottenham have made it clear that they are not willing yet another key player to leave the club this summer.