Unpressurized planes are generally operated without oxygen masks to about 8,000 or 10,000 feet above sea level. (Unpressurized cargo planes and unpressurized owner-flown planes are sometimes flown at higher altitudes with oxygen masks.) Pressurized planes are generally designed so that at their maximum altitude, the cabin will be pressurized not to sea level, but to about 8,000 or 10,000 feet. (If someone had a medical condition that required they not experience a pressure difference from sea level, it would be possible to charter a pressurized plane for them and fly it at a substantially lower altitude than it normally flies at and to keep the cabin pressure at sea level, but those planes generally get much worse fuel economy at the lower altitudes, and the weather at lower altitudes is often less smooth.)
I think Teluride has one of the few airports in the US where a pilot of an unpressurized plane likely needs an oxygen mask to land, and I suspect airports are more likely to exist at high altitudes than train tracks which are a part of the national rail system, so I suspect pressurized airplane cabins operate at lower interior pressure (higher effective altitude) than Amtrak trains.
I would think that creating a vacuum would be easier at higher altitudes, but that creating a particular pressure difference by reducing the pressure below atmospheric pressure would become more difficult.