What's the difference?

The Jewish concept of heaven or Olam Haba is different from the Christian concept of heaven for many reasons the main one, in my opinion, being that eventually everyone gets into Jewish heaven after compensating for their sins, including non-Jews.

Paying for thy sins!

The way that people compensate for their sins is going to hell, but don't worry it's not permanent. The length of your stay in hell is relative to how good or bad you were when you were alive. So if you were good you might be able to bypass it and if you were really bad you might have to stay there for a maximum of 12 months.

So what's hell like?

The Jewish concept of hell unlike the Christian concept of hell does not include devils with pitchforks. The Jewish concept of hell is best explained by the following legend:

Hell is a giant movie theater with only you and God sitting in the audience and the movie playing is a movie of your entire life. God watches all your good deeds and bad deeds and the embarrassment of God seeing everything you have done wrong is punishment enough.

OK so I'm done with hell where to now?

After a grueling trip to hell you will arrive at heaven and they say that a second in heaven feels as good as all the goodness you experienced when you were alive combined. I will describe heaven with the following legend:

Heaven is a big Yeshiva (school) and the teacher is God. The position of your seat in the classroom is relative to how good or bad you were when you were alive. So if you were really good you can get a front row seat for God's lessons and if you were really bad you might get stuck in the back.

Right now your probably thinking WTF I live my whole damn life only to end up back in that horrid place but don't worry it's just a legend not a definite fact. However, the pleasure that you get in heaven is relative to how good or bad you were in life this is best described by the following legend:

There are two heavens, one for the good people and one for the bad people, and both of them are exactly the same. In the heavens there is a huge all you can eat buffet with every type of food that could possibly exist the only catch is that instead of arms all the people in heaven have unbendable meter long forks. As you can imagine it would be very difficult to get food in your mouth if you had meter long forks instead of arms. In the heaven for the bad people the people are all starving trying to put food in their mouths but in the heaven for the good people the people are so used to being good that they feed each other.

That's it?

Yes, that's it. Once you're in heaven you can't change seats in God's classroom unless the people who knew you that are still alive , by doing good in your memory or by sitting Shiva (mourning you), get you brownie points with God. So make sure you teach your kids to give lots of charity!

Some points about Heaven and the other place..

Avraham's thoughts on Hell
The Midrash(I believe) says that Avraham was offered the choice between his children spending four hundred years of slavery in Egypt or his children spending time in Geyhinom. Avraham chose the slavery in Egypt because no matter how bad things get here in this world, they are a lot worse in Hell. Like getting dental work done without anesthetic, it's only going to take a little while, but you'd still do almost anything to avoid the dental work.

A little bit about the World to Come As explained by the Baal HaTanya.
There are two levels of Gan Eden, the garden of Eden, the upper and the lower. In the lower Gan Eden people's souls are nourished by smells, instead of by eating. Smelling the fruits and the plants and flowers replenishes one's neshama. In the upper Gan Eden, souls are nourished simply by seeing. The divine light of the Shekhinah shines and nourishes all the souls in the upper garden.

The Baal HaTanya also goes on to explain, quoting the Arizal, that mitzwoth performed in this world are the clothing of souls in Gan Eden. Torah, he explains, is the food of the soul in Gan Eden. He continues: The reason why the Rabbis say that learning Torah is comparable to performing all the mitzwoth in this world is because the Torah is also clothing for our soul in this world. So the Torah, in this world, is clothing, and, in the world to come, is also the sustenance of the soul. Whereas the mitzwoth are only clothes.

There's a whole different, deeper level. We wouldn't want you to think that the mitzwoth aren't important. In fact, the Tanya says just the opposite:
This world is actually a greater gift than the world to come, because in the world to come, as in all the upper realms, God is ultimately incomprehensible, unattainable, inaccessible. Down here in this world, we can unite ourselves with God so completely we are actually embracing Him. The mitzwoth are not only our clothes, but they are the clothes of God Himself. One of the points mentioned in the Tanya is that the six hundred and thirteen mitzwoth are the limbs and sinews of the King. It is something beyond our comprehension and yet paradoxically at the same time it is something we can grasp on to. By learning the depths of the mitzwoth and by embracing them in Thought, Speech, and Action, we can unify ourselves with God in a closeness not even attainable in heaven. True, he says, there are many many layers of clothing between our divine soul and God, but hugging a King is still hugging a King regardless of how many layers he's wearing, he's still in the clothes.

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_{corrections appreciated, especially regarding the story with Avraham, it may have been aggadata, I don't know.}