
Let me start this post by saying that kids should NOT learn to rely on a calculator to do their math for them. That said, a good calculator is a powerful tool for doing more complicated math and for performing tedious operations (after they have been mastered manually). Things that used to take mathemeticians all day to complete are being done routinely in high school classrooms around the world in a matter of seconds thanks to these little gizmos.
I am totally a fan of Texas Instrument Calculators. Almost all classroom teachers use them for demonstration, and they are by far the most popular among students. It is so hard to have different equipment than everyone elso around you, and Texas Instruments calculators are awesome anyway. The functions and placement of the buttons are as intuitive as they can be.
Another great thing about the TI series is that if you start out with a more basic calculator and upgrade as your math courses need you to, the functions don't change, there are just more of them. So, if you learn one of their scientific calculators, you'll be surprised at how much you already know how to do when you invest in a graphing calculator.
So long as students are using their calculators appropriately (read: they can do the math on their own, but use the calculator to check their work and speed up the process), here are the levels I recommend:
Elementary School (4th - 6th Grades)

TI-15 Explorer™ ($10 - $15)
What does an elementary school student need a calculator for? Nothing. However, it is imprtant to get familiar with the equipment, the same way you let your kids play computer games when they are younger, and then they know how to hack into your financial records by the time they're 10. The two line display is reason enough to give this calculator a try. Just make sure that they use it to verify and check, or to explore some higher level math concepts, and not as a shortcut to having good, solid, basic math skills. We all have to deal with fractions sometime!
Middle School (6th grade - pre-algebra)

TI-34 II Explorer Plus™ (Price $18-$23)
This is the middle school version of Ti's scientific calculator. It's an excellent training calculator. it pretty much does everything that the TI-36 does, but with the functions a middle schooler would need most often found on the the front (as opposed to under a menu). For example, there are lots of fraction functions that you would have to search for on the regular scientific calculator, but you have to search for trig functions (like sin, cos, tan), which would be found front and center on the TI-36.
High School, Scientific (Algebra, Geometry, and Algebra II, Chemistry and Physics)
High School students will not even find a graphing calculator
useful until Algebra II, and will not find it
neccesary until pre-calculus. These calculators are just enough power:

TI-30Xa (Price: $15-$20)
A super-basic scientific calculator. It can do all of the functions that a student through geometry and/or chemistry might need, but it doesn't have the 2-line display, so you can't see what you enter. That can be really confusing if you are entering more than a couple of operations. It's worth the few extra dollars for the TI-36X II.

TI-36X II (Price $20-$25)
Totally worth the extra $$$ compared to the TI-30. This is the most popular scientific calculator out ther, and there's a reason for it. It does everything a student taking math through alsgebra II and chemistry could ever need (except graphing), and it is very easy to use. The functionality is the same as the TI-83 and TI-84 graphing calculators, so when you finally decide to invest in the big calculator, you'll already know what to do. The two line display is great - you can see what you entered, and even edit it afterwards. This is absolutely my personal pick for a scientific calculator.

TI-36X (Price $20-$25)
This calculator is sleek and pretty, and has a few extra goodies, however it does not have the 2-line display. This alone makes the TI-36X II a better pick for about the same price.
High School, GraphingHigh School students will not even find a graphing calculator
useful until Algebra II, and will not find it
neccesary until pre-calculus. These calculators are a must for any pre-calc, trig, or calculus students, and are worth the investment. Just make sure you give them a lecture about not
losing these beauties, they're not cheap:

TI-83 (Price $99 - $129)
This graphing calculator is the standard. Everything you need, and if you get the "Plus" edition, you can hve a little more memory and even link to other other calculators to share extra programs. The thing is, that for about $10 more, you can get the upgraded version of the TI-83 - the TI-84, so you should.

TI-84 (Price $109 - $139)
This calculator is
Just Right. This would definitely be my pick for a graphing calculator for a high school student. It has all the power you could need, and is still easy and intuitive to use, and it is permitted on all of the usual standardized test out there that allow a calculator. It is just like the TI-83, except you get a lot more memory and linking capability, including a USB cable for downloading even more "educational" software. Oh, and it comes in fun, funky colors and you can even get removable faceplates for it, just like your cell phone!

TI-89 (Price $119 - 149)
This calculator is so much power, it's confusing to use, and it's way different thatn the other TI calculators, so your teacher won't know how to use it either. There are no additional functions that a high school student could ever use compared to the TI-84. Don't buy this calculator just because it's the "top of the line." It is, if you're studying math or a physical science in college. For high school, stick to the TI-84.
All of these calculators are available at Office Depot, Staples, and Target. be sure to shop those back to school sales!
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