Which Jazz Albums are similar to Kind of Blue

There have been some excellent suggestions made here. I would also recommend recordings from the same era from Harold Land, Benny Golson, Tina Brooks, Kenny Dorham, Art Pepper. If you're looking for a really "cool" and laid back sound, you must check out "Blue Hour" on vinyl or "The Complete Blue Hour Sessions" on CD...Stanley Turrentine w/ The Three Sounds.

Here is another one Way Out West by Sonny Rollins

KOB was released in 1959 -The Best Year in Jazz History-
Miles Davis
Dave Brubeck
Charles Mingus
Ornette Coleman
...and other honorable mentions.

all released Jazz masterpieces.

I agree with all previous "evident suspects" simply because I got most of the albums as LPs or XRCDs.
My five cents (rather a million-dollar advise, posted here for free!):
Khmer by Nils Petter Molvaer, if you love Miles you will love this album.
also, ECM released a lot of "must-have" albums since 2006

If you listen to the first cut on "Kind of Blue" carefully, you'll discover that in the beginning, before  Cannonball Adderly takes his solo, what you are listening to is an average studio recording. Good jazz players to be sure. Who could take issue with Miles and Coltrane? However, once Adderly takes his solo, he is so inspired that he brings the rest of the group to attention and from then on, its a great album. So, to answer your question. buy more albums that feature Cannonball Adderly. 

OP