Links between the Blues and Chilwell have been persistent for months, with manager Frank Lampard keen to upgrade his options on the left side of his defence.
Marcos Alonso was impressive in his role as a wing back under Antonio Conte but has been exposed defensively in recent years, while his attacking contributions have also dried up. Emerson Palmieri has also failed to take his opportunities when they've come, with Lampard never convinced by either player.
It's been confirmed to 90min that the deal is worth over £50m. It's down from the £75m Leicester quoted Chelsea and Manchester City a few months ago, due to the Covid-19 pandemic and the Foxes' failure to qualify for the Champions League.
Chelsea have been in contact with Leicester since January over Chilwell, who has always been Lampard's first choice target at left back. There is a broad agreement between the two clubs, with personal terms all but finalised.
A Chelsea source told 90min: “Frank is very happy that his ideas are being listened too, and the club are backing him in this manner – he knows he needs to produce the results, but he is confident he can and the club clearly believe he can too.”
Chilwell missed the end of last season due to a heel problem but has had medical checks in London and is only expected to be out of action for another three weeks. Leicester have a number of options they're looking at as replacements, with Arsenal's Kieran Tierney at the top of Brendan Rodgers' list.
Chelsea had previously faced competition for Chilwell's signature from Manchester City. Pep Guardiola's side have spent bucket-loads on defenders in recent years but still don't have a reliable option at left back.
However, the Citizens have so far failed to move on Benjamin Mendy and the club's hierarchy could not justify signing Chilwell with the Frenchman still at the club.
The window is shaping up to be a good one for the Stamford Bridge outfit. Hakim Ziyech was confirmed as a Chelsea player earlier in the window, while Timo Werner ditched RB Leipzig for the Blues in June.
Chelsea are still rivalling City for Napoli defender Kalidou Koulibaly and they're not too far off finalising a deal for Bayer Leverkusen's Kai Havertz, with the asking price the only sticking point after personal terms were agreed.