Some people have said this but anyways...this project will hapen, the only question is if its going to be sooner or later. Also when this project final hapens it wont include a highway and it wont include highspeed rail, this i can gurantee. This project will be most likely a two rail tunnel for freight, with a pricy train or two a day for pasengers...and obviously it will include pipelines etc.
Edit: I did a quick map to show how useful a link via the bering sea would be. Just imagine the transport of goods from asia to north america and even south america and vice vesa at 10 times the speed and a fraction of the cost? The Bering strait actualy would have almost the most direct conection between China-Asia and North Amrican-South America.
One more adition, i just noticed that the straight line right through directly links the midle east and the east coast of america, some might think this is bad and sure it would be a even biger undertaking building up pipeline capacity along the coridor through various countries, but just imagine the profits that this tunnel would generate. I real think its a no brainer, the only thing holding it back is politics and the complexity of it. Also think of the enviromental benefits of taking thousands of ships of the ocean.