Rossonero vice-president Adriano Galliani met with Ancelotti in Spain on Tuesday evening, less than 24 hours after his sacking by Real Madrid.
Despite Ancelotti’s declaration that he would take a year off from coaching if let go by Real, Milan are persisting.
“I am here to bring Ancelotti back to Milan,” Galliani said to Italian media. “I will not give up.
“I told him to say yes. There will be another meeting tomorrow (Wednesday).
“I am here to get him to return to Milan and tomorrow the pressing continues.”
Ancelotti is one Milan’s most successful coaches, having led the Rossoneri to the 2004 Serie A title and two UEFA Champions League crowns.
“The negotiations with him are always good as he’s part of our family,” Galliani said. “We won 11 international trophies together and he is in our history.
“I met him for the first time in 1987 and there is an excellent rapport between us.
“This is one of those relationships that never ends. Carlo knows that, if he doesn’t say yes I will fly with him and his wife to Vancouver!”
Ancelotti, who led Real to a 10th European Cup title in June 2014 but failed to win the league in his two seasons in Madrid, is expected to fly to Vancouver on Friday.
The 55-year-old is set to have a back operation in Canada this summer.
Ancelotti left Milan in the summer of 2009 to join Chelsea after eight successful years at the helm of the Rossoneri outfit.
Milan are keen to bring Ancelotti back after two hugely disappointing campaigns.
The Rossoneri, under first-year coach Filippo Inzaghi, can finish no higher than eighth in Serie A this season and will miss out again on European football.
“If Ancelotti decides to return to us, we are tied by a great past and great respect and personal affection,” AC Milan president Silvio Berlusconi said.
Milan end the campaign at Atalanta on Sunday.