The best way to imagine what the hell i'm trying to describe here is this... please try

Think of 2 syringes (empty) placed opposition each other, the 2 pins meeting, now let's large it up to scale, the needle becomes a tube in which a bullet shaped cabin sits to transport 20 - 30 people or so at a time.
[ ]~~~~~~~~~~~~~~~~~~~~~~~~~~~[ ]
[Compressed Air]=========[Transport]=========[compressed air]
[ ]~~~~~~~~~~~~~~~~~~~~~~~~~~~[ ]
[transport] is simply the place passengers can sit and buckle up

From 1 location to another, firing the transport bullet very quickly, when it gets to the destination the air inside the other air tank is also being compressed which in turn slows it down, just before it gets too slow some kind of tractor grabs it (like at any theme park ride) and pulls it in to help compress the tank further (taken over by power electric), the passengers get out, the new ones get in, 30 seconds later shot out of a high velocity air cannon back in the other direction.
So could this in theory work?