Chelsea’s Brazilian midfielder Oscar helped the blues by scoring a double brace in the second-half.
Over 64,000 people showed up to see the Blues face the fallen Italian giants in Minneapolis, Minnesota.
Chelsea took the lead with a 24th minute goal from Bertrand Traore, howver, Milan equalised just before half-time with Giacomo Bonaventura scoring the goal.
Milan looked more comfortable and dominating in the first-half, as the Rossoneri took control of the game.
But, Chelsea came back strong in the second-half as the rejuvenated Blues were awarded a penalty after Andrea Poli handed a cross from Cesar Azpilicueta.
Chelsea’s playmaker Oscar stepped forward to take the shot and scored from the deadball situation.
Oscar doubled his tally, late in the game when he snuck the ball past Milan’s Wonderboy goalie Gianluigi Donnarumma.
Milan started the game strongly, and came very close to scoring, but Ignazio Abate’s attempt was denied by Thibaut Courtois.
The big Belgium looked more like himself in this game, after having a disastrous 2015/16 campaign.
Courtois made another fantastic save just before Chelsea’s opening goal, when he denied Mbaye Niang.
Traore then captialised, when Victor Moses shot was blocked by Donnarumma, but Bertrand found the ball on the rebound and put it inside Milan’s net.
Milan were put back in the game by a Bonaventura stunner, as the Italian found the back of the net with a free-kick.
Chelsea boss Antonio Conte introduced Eden Hazard and N’Golo Kante in the second-hald, and the Belgian got off to a flying start, as he gifted Willian a goal on the platter, but the Brazilian was denied by Donnarumma.
However, Oscar managed to comfortably win it for the London based club after a 87th minute goal.
Chelsea will face German team Wreder Bremen, while Milan face Freiberg in their pre-season friendlies.