How to make a CD Jacket and print out Song order directly from playlist

There is a pretty basic CD insert that you can print from iTunes, if I remember correctly it will print whatever artwork is attached to the first song in the playlist.
Open iTunes, highlight the playlist in question, go to File>Print and choose the CD Jewel Caser Insert radio button. Theres also a little Theme menu.

However you can get much more flexibility from a dedicated CD Cover program. I use Cover Star, it's inexpensive and makes good quality CD booklets, back covers and disc overlays. It will generated artwork for you or you can drag your own picture files to it. You can download a trial version from this link: http://autostylus.com/coverstar.html. It's fully functional apart from printing so you can play around with it and save the inserts until you decide if it's for you. Purchasing a license then releases the final function and anything you saved previously can be printed off.

Select the playlist, go to file menu>Print. Choose the CD jewel case insert and a mosaic Theme. It will do exactly what you wondered.