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So if you make a flyng monster prone it falls. What if it falls ON a player character or another monster?

A flying monster could also choose to go prone to deliberately dive bomb a smaller / weaker opponent.

In both cases the falling monster takes damage but what about a character it chooses to or happens to land upon?

Seems to me that should take just as much damage. 

 By RAW, nothing happens - the monster lands in the character's square, not on the character.
Deliberately crash-landing on an opponent, from a theoretical point of view, would definitely require an attack roll, most likely against their Reflex.  Damage would be entirely arbitrary, since the rules don't cover the situation at all.

RAW nothing happen if a creature falls in the same space as another one. This is if it can in the first place since a creature cannot enter its enemy's space unless it is Helpless, tiny or two size category smaller or larger and it cannot enter an ally's one unless its tiny or prone. 

RC 205 Occupied Square: A creature cannot enter an enemy's space unless that enemy is Helpless or two size larger or smaller than it. A creature can enter an ally's space, but it can end its move in an ally's space only if the ally is prone.

Does that mean that you stop a square in the air?

Personally i think 1/2 the falling damage to each is reasonable.

It means it'd fall in a square adjacent unless there is none it can enter, and if so, then RAW doesn't cover how to handle it. 

If a medium creature would fall in a 5 feet large shaft with an enemy at the bottom and no where to fall adjacent, a DM could allow the falling creature to share space with its enemy anyway or have both of them become Helpless until they don't share spaces anymore for exemple.

As for damage, falling into a square occupied by another creature doesn't deal damage to her, most likely because it doesn't necessarly land on her since a creature doesn't fill the square in its space.

RC 200 Filling a square: Unless otherwise noted, a creature or an object such as a chair does not fill squares in its space.

Nov 24, 2012 -- 4:01PM, D-Mar wrote:

A flying monster could also choose to go prone to deliberately dive bomb a smaller / weaker opponent. 

This could be handled as a DMG p.42 stunt. Or more easily: as a refluffed normal attack (charge, melee attack, etc.).

It's not handled by RAW so DM's call.  Perhaps refluff it as a Charge/Bull Rush attack.  But the attacker cannot occupy the target's square no matter what so have him end up in an adjacent square.

Keep in mind if the monster falls, intentionally or not, it could end up taking damage when it hits the ground or the target.  Could this result in the attacker taking more damage than the target?  Sure!  Making yourself fall intentionally is usually a bad idea anyway!

But yeah, it's not really handled by the rules so pretty much DM's call.      

I'm not aware of anything RAW on this. I usually give the creature landed on a few dice of damage (1d10 heroic, 2d10 paragon...ish) and slide the landed on creature out of the space if there is an available spot...but that's totally a houserule.

This falls under Keith's Law: Expect Table Variation