Which Jazz Albums are similar to Kind of Blue

Agree with Henry, great call. Another one I would recommend is Herbie Hancock's Maiden Voyage. It doesn't actually sound like KOB, but it is similarly accessible and lyrical with spare arrangements and wonderful playing. The young Herbie along with the young Freddie Hubbard, the very young Tony Williams (whose brilliance is abundant on this record), and George Coleman and Ron Carter. It's a jazz album that has managed to penetrate my DNA in almost the same way KOB has.

anything with Ben Webster will likely give you a bit of that ease and magic. Ben has that combination of 'cool jazz' but with great tone and subtle energy that Miles had in KOB. Ben is my favorite Sax player.

i particularly like 'At the Renaissance'.

'Chet' from Chet Baker is another winner in that same vein.

Within Miles, try Round About Midnight

Another artist you may like is Philip Catherine. While he's not really like Miles "Kind of Blue", I think he appeals to those who like that genre. I would start with 1) "Transparence", and 2) "Philip Catherine/Bert Joris Brussels Jazz Orchestra - "Meeting Colours" ; but, really anything by him is worth having.

The Cannonball Adderly offerings with Bill Evans and Milt Jackson are must haves. Now they are more boppin than KOB but if you buy the re mastered extended CD's the sound will not disapoint.