Although I had a lot of experience with CAD programs, I struggled with Illustrator 8. I finally upgraded to v. 10 and bought Classroom In a Book for that version. You CAN teach yourself Illustrator with the manual and this book in a few weeks. ICIAB is a good supplement to the manual, which for reasons that always baffled me, has too few illustrations for information aimed at visually oriented people.
You will have to do some experimentation to get full benefit from the lessons, but I picked up things I was clueless on before. It does help to have some additional book such as Visual series (PeachPit Press) for details not covered.
Downside: some errors of tools or keys, nothing serious. But I was disappointed by two topics; the web chapter separately covers making a Flash animation for the web, and slicing a graphic for the web, but while the "finished" version of the lesson shows both in a complete web page, the lesson doesn't tell you how to put them together without the Adobe Web program (too expensive for me). You have put both html files in a text editor and combine them using the complete example for reference as to where to put the Flash file and what to include or leave out.
Also, the section in lesson 6 on data/variable objects is applied in a page of business cards, but doesn't explain how to get the data base and variable fields applied to all incidences of the biz cards on the sheet. I did figure it out for myself, but it took me about an hour of experiment, and is almost as tedious as just editing the file, though once the database is set up it would be quick to print out new cards with the variations.
But overall, a really good way to learn Illustrator to an intermediate level, and a whole lot cheaper than any class I've looked into (plus classes tend to be taught on MACs in my area).