If I use I tunes match and have all my music on the cloud, will I be able to listen to it, meaning will it be on my device when I am without a cell or wifi signal....like on a plane or in an area without service?

Yes, it would count against your data. The transfer part is part of your cellular coverage, whether it be from Apple's iCloud or a totally unrelated feed.

iTunes match - http://www.apple.com/itunes/itunes-match/ - see FAQ at end too

"Does iTunes Match stream or download songs?

On a computer, any songs stored in iCloud will stream over the air when played, though you can download them at any time by clicking the iCloud download button. iOS devices will start playing tracks from iCloud as they download and will store them so that you can listen to them later even if you don’t have a network connection. Apple TV only streams songs."

So, from the above, if you are sitting in an airplane and suddenly decide you want to listen to a song that has not downloaded to your device then you will have to wait until you can use your service again (or pay the airline to use their wireless).