how does oil get into the engine combustion chambers?

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Has to come in either through the top or the bottom I imagine. So your post pretty much covers it. The only other way I can think of is on cars with mechanical fuel pumps. If the diaphram is bad you can get oil in the gas and vise versa.
 
oil can be coming past the piston rings if they are shot, or down through the valve seals/guides. Also, if you have a pcv valve issue and were sucking in through your intake.
 
alright thank you, i just had some heads rebuilt because my mechanic said that was the problem, i also know one of the spark plugs gets oily so it could be the piston ring, my dad said get a compression test so i can find out whether its the ring or the heads, thanks!
 
a leak down test is best for checking the source of a leak. dry and then wet compression tests can help a bit too (though not nearly as much).
 
Sirsureshot, your dad, and hissin have you covered on this one. Leak down will tell you if it's rings, or a bad valve/seat seal. Unfortunately, it won't tell you if it's a guide or valve stem seal. The actual symptoms will nail those down. Guides will usually make noise, and blue smoke will be seen on start up (and go away after the engine warms a bit). Guides and/or stem seals may show blue smoke upon deceleration - as heavy vacuum in the cylinder can pull oil from the head past the seals or a loose guide. So, if your leakdown test tells you the rings are sealing, and you've got the smoking symptoms above, it's likely guides and/or seals.

Oh - if you've got problems with valve to seat sealing (like a burnt exhaust valve for instance or bent valve stem), the leak down test won't tell you anything about the rings in that cylinder. The pressure will find the path of least resistance (usually past the bad valve seat) and you won't get an effective ring test cause the valves won't hold the pressure in.
 
dont know about the prices. you can make a leakdown tester. i think Jrichker has a link to make one on his site.

dry compression tests check baseline/relative compression - the wet component checks rings by comparison to the dry numbers (and thus can be used as a crude elimination device).
good luck.