Sky Italia are reporting that the 26-year-old Colombian is still in Italy but due to fly to London on a private jet on Saturday morning at 7am for talks and a medical at Stamford Bridge.
Fiorentina are expected to receive £23.33m plus a bonus that amounts to Cuadrado's £26.34m release clause with Chelsea's out-of-favour forward Mohamed Salah moving on loan in the opposite direction.
When asked about Cuadrado's potential move to the Premier League leaders, Montella told his club's website on Friday: "It was a sale that had to be done. The club has done the right thing because we are also getting a very good player.
"Naturally, we need to understand how long Salah will need to adapt to our football as it's different from the English and Swiss leagues.
"From a defensive standpoint, Cuadrado guarantees us a lot more than Salah. Cuadrado is a player that has always arrived with a smile and given everything to Fiorentina.
"I am convinced that if he could have played tomorrow he would have. I'm happy for him because he is going to a big club."
On whether Fiorentina have been weakened by the deal: "We’ve lost a top player but I see similar characteristics in Salah. I don’t think it’s a step backwards."
Cuadrado, viewed by Chelsea as a replacement for forward Andre Schurrle who's closing on a move to Wolfsburg, joined Fiorentina in 2012 from Udinese and has been a regular in Montella's side since.
The Colombian has scored four goals and set up four more in 17 league appearances for the Serie A side this season.
He was one of the stand-out players alongside James Rodriguez for Colombia in last year's World Cup in Brazil and was tied to the Viola until June 2019.
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