It's important to look at the hyperloop in the context in which it was proposed. This is California and environmental aspects need to be taken into account. Airlines are a major source of CO2 and California wants a more environmentally friendly solution. There is a proposed high-speed rail project with a $10B initial estimate that's sure to at least double by the time the project is complete. The high-speed rail project is only high-speed compared to existing rail since the max speed will be around 200 mph.
It's into this environment that Musk proposed the Hyperloop. On paper, it's better than the high-speed rail in every way. Cheaper, faster and with less pollution. The "more airplanes" alternative may be cheaper and probably faster (with the TSA is doing its best keep air travel slow) but fails horribly on the CO2 emissions front.