If you have Windows 8, you can do the following:
Go to Album/Song view (doesn't work in Artist view for no apparent reason)
Right-click an album
In the bar at the bottom of the screen, click Match Album Info (you might have to click the three dots to access the extra options)
Follow the steps to find the right album
If done correctly (and if the songs are actually streamable from the cloud; not all are, for example red hot chili peppers if I remember) a little picture of a cloud should appear next to your album. This states that it is in your cloud collection and is available to stream/download to other devices.
Check out
http://m.winsupersite.com/article/windows8/windows-8-tip-match-music-144730 for a more in-depth guide.
One thing you should be aware of: you are not uploading, but matching to songs already in the cloud. So if you have, say, a live version which is not in the cloud, your best option would be to simply upload it to SkyDrive using the SkyDrive app, though I'm not sure whether that's technically allowed under the terms and conditions.