1. 90% of the time it's cheaper to buy online, then in the store. Amazon.com is usually the best choice. But the price difference online is always very small. Other factors start to matter: customer experience? easy of navigation, free shipping, etc.
  2. If you want to pay the lowest price 100% of the time - shop around. Don't limit yourself to just one store. Good thing you don't have to lift your bottom from the chair to find the best deals nowadays. You will just need a computer mouse and 5 minutes of your time. Even brick and mortar stores have online stores (they even have local ads with coupons that you get in your mailbox)
  3. Amazon.com usually beats everyone with price. Newegg.com is my second favorite
  4. Try Google shopping http://www.google.com/prdhp or www.pricegrabber.com who search many stores at ones for you. You need to know what you are looking for beforehand, since you can't really browse in different categories and see what looks good or is the most popular product in the category. Also, you may get confused by same product having multiple listings or different names… I really suggest you stick to amazon.
  5. If you are a student (or were a student recently) you are in luck! Many companies that sell expensive software offer stuff to students for much smaller price (Ex. Microsoft -Windows, Office or Adobe - Photoshop). Sometimes all you need is have a school email (that ends with .edu instead of .com), but sometimes you will need to scan and send them some documents (student ID, schedule)
    www.academicsuperstore.com
    www.journeyed.com/
  6. What about your usual stores like bestbuy? The prices there are usually higher. But when they have something on sale (check local ads) it may be worth checking out. Unfortunately such deals for software are very rare. They usually have electronics on sale.
  7. Check the company that develops the product. It's still usually cheaper on amazon, but they may have a promotion.
  8. If a new version is coming up soon you may preorder for cheaper (usually stuff like windows or office).
  9. Do you have to buy software or can you use a free, legal alternative? Please see my list of free software alternatives to most used programs.
  10. Most of software you can get illegally for free and save hundreds or even thousands of bucks (Adobe stuff costs are through the roof). Check out my guide.